N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-propionamide → N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-propionamide

HRID 1784845Notes

Reaction equation

HRID 1784845 reaction equation
BrC1C=C(NC(=O)CC)C=C(C(C2C=NC=CC=2)=O)C=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:29]2[CH:30]=[C:31]([NH:54][C:55](=[O:58])[CH2:56][CH3:57])[CH:32]=[C:33]([C:35]3[CH:43]=[CH:42][CH:41]=[C:40]4[C:36]=3[CH:37]=[CH:38][N:39]4[Si](C(C)C)(C(C)C)C(C)C)[CH:34]=2)=[O:28])[CH:22]=1>>[NH:39]1[C:40]2[C:36](=[C:35]([C:33]3[CH:32]=[C:31]([NH:54][C:55](=[O:58])[CH2:56][CH3:57])[CH:30]=[C:29]([C:27]([C:23]4[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=4)=[O:28])[CH:34]=3)[CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:38]1

Participants

3

Reactant 2

HCID 68844539N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-propionamideHCID 68846779N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-propionamide

Product 1

HCID 15602990N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-propionamide

Procedure

N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-propionamide was converted to N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-propionamide, and the triisopropylsilyl group was removed with tetra n-butylammonium fluoride to give N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-propionamide as described in Example 35. 1H NMR (400 MHz, DMSO-d6): δ 11.30 (s, 1H), 10.20 (s, 1H), 8.95 (s, 1H), 8.82 (d, J=3.5 Hz, 1H), 8.32 (s, 1H), 8.17 (d, J=7.8 Hz, 1H), 8.02 (s, 1H), 7.66 (s, 1H), 7.60 (dd, J=7.7, 5.0 Hz, 1H), 7.45-7.41 (m, 2H), 7.17 (t, J=7.6 Hz, 1H), 7.10 (d, J=6.6 Hz, 1H), 6.62 (s, 1H), 2.35 (q, J=7.5 Hz, 2H), 1.08 (t, J=7.6 Hz, 3H).

Workup

  1. customthe triisopropylsilyl group was removed with tetra n-butylammonium fluoride

Sources & evidence

ORD record
ord-c072a979a3cd4577b6994bb033b47d10
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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