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

HRID 2365426Notes

Reaction equation

HRID 2365426 reaction equation
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CON(C)[C:13]([C:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:17]([Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH:16]=1)=[O:14]>>[C:2]1([CH2:1][C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17]([Si:24]([CH:28]([CH3:30])[CH3:29])([CH:31]([CH3:33])[CH3:32])[CH:25]([CH3:26])[CH3:27])[CH:16]=2)=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 86707831N-Methoxy-N-methyl-1-Triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamideHCID 178418336HCID 178418336, compound

Product 1

HCID 867078322-phenyl-1-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanoneYield 92%

Procedure

This compound was prepared by the reaction of benzylmagnesium chloride (2.0 M solution in THF) 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 92% yield as a light yellow viscous oil.

Sources & evidence

ORD record
ord-80dc15e6c9b34509a8d981cdfb7c8680
Source dataset
uspto-grants-2014_04
Patent number
US08697697B2

Reaction notes

Loading…