Methanesulfonyl chloride → 5-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

HRID 595564Notes

Reaction equation

HRID 595564 reaction equation
[NH2:1][C:2]1[C:28]([Br:29])=[CH:27][C:5]2[C:6]([C:23]([NH:25][CH3:26])=[O:24])=[C:7]([C:9]3[CH:10]=[N:11][C:12]([O:15][C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=4)=[CH:13][CH:14]=3)[O:8][C:4]=2[CH:3]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Br:29][C:28]1[C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:3][C:4]2[O:8][C:7]([C:9]3[CH:10]=[N:11][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)=[CH:13][CH:14]=3)=[C:6]([C:23]([NH:25][CH3:26])=[O:24])[C:5]=2[CH:27]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 903325546-amino-5-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methylbenzofuran-3-carboxamide

Product 1

HCID 903324665-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamideYield 85.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a degassed solution of 6-amino-5-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methylbenzofuran-3-carboxamide (100 mg, 0.22 mmol) and DMAP (10 mg, 0.02 mmol) in Pyridine (5 ml) under N2 was added MsCl (32 mg, 0.38 mmol) at 0° C. Then it was stirred at 20° C. for 15 h. The reaction mixture was concentrated and extracted with DCM. After it was washed with brine, dried over Na2SO4 and concentrated, the residue was purified by prep-TLC to give 5-bromo-2-(6-(4-fluorophenoxy)pyridin-3-yl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (100 mg, yield: 85%). 1H-NMR (CDCl3, 400 MHz) δ 9.65 (s, 1H), 8.73 (s, 1H), 8.54 (d, J=4.8 Hz, 1H), 8.39 (d, J=2.8 Hz, 1H), 8.03 (s, 1H), 7.84 (s, 1H), 7.33˜7.38 (m, 4H), 7.28 (d, J=8.8 Hz, 1H). (M+H)+: 534/536.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with DCM
  3. washAfter it was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-134be53dbcc74a9492422072608fc8bb
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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