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

HRID 1784840Notes

Reaction equation

HRID 1784840 reaction equation
BrC1C=C(NS(C)(=O)=O)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][S:55]([CH3:58])(=[O:57])=[O:56])[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][S:55]([CH3:58])(=[O:56])=[O: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 50994356N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-methanesulfonamideHCID 50994434N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-methanesulfonamide

Product 1

HCID 15602988N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-methanesulfonamide

Procedure

N-[3-bromo-5-(pyridine-3-carbonyl)-phenyl]-methanesulfonamide was converted to N-[3-(pyridine-3-carbonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-methanesulfonamide, and the triisopropylsilyl group was removed with tetra n-butylammonium fluoride to give N-[3-(1H-indol-4-yl)-5-(pyridine-3-carbonyl)-phenyl]-methanesulfonamide as described in Example 75. 1H NMR (400 MHz, methanol-d4/CDCl3): δ 8.97 (s, 1H), 8.71 (s, 1H), 8.14 (d, J=7.8 Hz, 1H), 7.87 (t, J=1.8 Hz, 1H), 7.78 (t, J=1.5 Hz, 1H), 7.56 (t, J=1.9 Hz, 1H), 7.44 (dd, J=7.8, 4.9 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.22 (d, J=3.1 Hz, 1H), 7.17 (t, J=7.7 Hz, 1H), 7.09 (d, J=7.3 Hz, 1H), 6.60 (d, J=3.3 Hz, 1H), 3.00 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-71213a03d6714097ba2c1921778420ef
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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