5-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide → 5-(6-(4-fluoro-1H-indol-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 1776826Notes

Reaction equation

HRID 1776826 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:25]2[C:26]([N:45]([CH3:50])[S:46]([CH3:49])(=[O:48])=[O:47])=[CH:27][C:28]3[O:32][C:31]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)=[C:30]([C:40]([NH:42][CH3:43])=[O:41])[C:29]=3[CH:44]=2)=[N:13][C:14]=1[C:15]1[NH:16][C:17]2[C:22]([CH:23]=1)=[C:21]([F:24])[CH:20]=[CH:19][CH:18]=2)C1C=CC=CC=1>CO.[Pd]>[F:24][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[CH:23]=[C:15]([C:14]1[N:13]=[C:12]([C:25]3[C:26]([N:45]([CH3:50])[S:46]([CH3:49])(=[O:48])=[O:47])=[CH:27][C:28]4[O:32][C:31]([C:33]5[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=5)=[C:30]([C:40]([NH:42][CH3:43])=[O:41])[C:29]=4[CH:44]=3)[CH:11]=[CH:10][C:9]=1[OH:8])[NH:16]2

Participants

4

Reactant 1

HCID 712954695-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Product 1

HCID 712954715-(6-(4-fluoro-1H-indol-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamideYield 57.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (120 mg, 0.173 mmol) and Pd/C (20 mg) in methanol (10 mL) was stirred under H2 atmosphere at room temperature for 1 hour. The mixture was then filtered through Celite and concentrated to provide 5-(6-(4-fluoro-1H-indol-2-yl)-5-hydroxypyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (60 mg, yield: 57.7%). 1H-NMR (Methanol-d4, 400 MHz) δ 7.95˜8.00 (m, 4H), 7.80 (s, 1H), 7.37 (t, J=8.8 Hz, 2H), 7.22˜7.30 (m, 4H), 6.64˜6.69 (m, 1H), 3.23 (s, 3H), 2.94 (s, 3H), 2.90 (s, 3H). MS (M+H)+: 603.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b4011c718e2d423a8a959a65b4fac5cb
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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