N-Methoxy-N-methyl-1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide → 2-(3-chlorophenyl)-1-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone

HRID 2365425Notes

Reaction equation

HRID 2365425 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[CH2:5][Mg]Cl.CON(C)[C:14]([C:16]1[C:24]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:18]([Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH:17]=1)=[O:15]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:14]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[CH:22][CH:23]=3)[N:18]([Si:25]([CH:29]([CH3:31])[CH3:30])([CH:32]([CH3:34])[CH3:33])[CH:26]([CH3:27])[CH3:28])[CH:17]=2)=[O:15])[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 86707831N-Methoxy-N-methyl-1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamideHCID 178478996HCID 178478996, compound

Product 1

HCID 682963382-(3-chlorophenyl)-1-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanoneYield 94%

Procedure

This compound was prepared by the reaction of 3-chlorobenzylmagnesium chloride (0.25 M solution in diethyl ether) with N-methoxy-N-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide as described in General Method 1. The desired compound was obtained in 94% yield as a viscous clear oil.

Sources & evidence

ORD record
ord-1156817d0c09488796b1f4a4bfaba64b
Source dataset
uspto-grants-2014_04
Patent number
US08697697B2

Reaction notes

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