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

HRID 1784838Notes

Reaction equation

HRID 1784838 reaction equation
BrC1C=C(NC(=O)C)C=C(C(C2C=NC=CC=2)=O)C=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:28]2[CH:29]=[C:30]([NH:53][C:54](=[O:56])[CH3:55])[CH:31]=[C:32]([C:34]3[CH:42]=[CH:41][CH:40]=[C:39]4[C:35]=3[CH:36]=[CH:37][N:38]4[Si](C(C)C)(C(C)C)C(C)C)[CH:33]=2)=[O:27])[CH:21]=1>>[NH:38]1[C:39]2[C:35](=[C:34]([C:32]3[CH:31]=[C:30]([NH:53][C:54](=[O:56])[CH3:55])[CH:29]=[C:28]([C:26]([C:22]4[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=4)=[O:27])[CH:33]=3)[CH:42]=[CH:41][CH:40]=2)[CH:36]=[CH:37]1

Participants

3

Reactant 2

HCID 50994355N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-acetamideHCID 50994433N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide

Product 1

HCID 15602989N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-acetamide

Procedure

N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-acetamide was converted to N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide, and the triisopropylsilyl group was removed with tetra n-butylammonium fluoride to give N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-acetamide as described in Example 35. 1H NMR (400 MHz, methanol-d4): δ 10.61 (s, 1H), 8.94 (s, 1H), 8.70 (s, 1H), 8.13-8.19 (m, 2H), 7.99 (s, 1H), 7.74 (s, 1H), 7.49 (s, 1H), 7.37 (d, J=8.0 Hz, 1H), 7.25 (s, 1H), 7.13 (t, J=7.7 Hz, 1H), 7.06 (d, J=7.0 Hz, 1H), 6.62 (s, 1H), 2.12 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-48100cc199564a2dbe594161ff885133
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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