Process for preparing n-benzyl indoles

Details Process for preparing n-benzyl indoles Process for preparing n-benzyl indoles

C - Chemistry, Metallurgy

07

D

C07D 401/14 (2006.01) C07D 209/08 (2006.01) C07D 403/14 (2006.01) C07D 413/14 (2006.01) C07D 417/14 (2006.01) C07F 7/10 (2006.01) C07F 9/6558 (2006.01)

Patent

CA 2190682

A process for producing a compound of the formula Image (I) in which R1 is hydrogen, halo, C1-4 alkyl, C1-4; alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C1-4 alkyl, aldehyde, -CH2Z, -CH=CH-Z or -CH2CH2Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R~ is halo, nitrile, an optionally protected acid group or -CONR7R8 where R7 and R6 are hydrogen or C1-4 alkyl; R4 is C2-4 alkyl, or C2-4 alkyl substituted by -CONR7R8 or an optionally protected acid group; R5 is Image Image Image or Image where W is -CH=CH-, -CH=N-, -N=CH-, -O- or -S-, R9 is hydrogen, halo, C1-4, alkyl, C1-4 alkoxy or trihalomethyl, and R10 is hydrogen, C1-4 alkyl, C2-6 alkenyl, C3-6 cycloalkyl or C1- 4 alkyl-C3-6 cycloalkyl; R6 is hydrogen or C1-4 alkyl; X is -O-(CH2)nCR11R12-, -CR11Rl2-, -CR11R12- (CH2)n.CR13R14- or -CR11=CRl2- where R11, R12, R13 and R14 are each hydrogen or C1-4 alkyl, and n is 0, 1 or 2; and Y is -O-CR15R16-, -CR15=CR16- or -CR15R16. CR17R18- where R15, R16, R17 and R18 are each hydrogen or C1-4 alkyl; or a salt thereof, comprising the step of reacting a compound of the formula Image (II) with a compound of the formula Image (III) to form a compound of the formula Image (IV) wherein R2a is selected from the groups recited above for R2, or R2a-X- is a protected hydroxyl group, and Z is a group of formula -Y-R5 recited above, or a group that can be converted into a group of said formula -Y-R5. Intermediates of formula IV and composition containing substantially optically pure enantiomers of Formula (I) are included within the scope of the invention.

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