Methanesulfonyl chloride → HCID 90332963, compound

HRID 595593Notes

Reaction equation

HRID 595593 reaction equation
[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12]([NH:14][CH3:15])=[O:13])=[C:7]([CH:9]3[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl.N1C=CC=CC=1.O>[Br:18][C:17]1[C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:3][C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[C:6]([C:12]([NH:14][CH3:15])=[O:13])[C:5]=2[CH:16]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 90332500HCID 90332500, compound

Product 1

HCID 90332963HCID 90332963, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
25 °C

Procedure

To a degassed solution of 6-amino-5-bromo-2-cyclopropyl-N-methylbenzofuran-3-carboxamide (4.0 g, 13 mmol) in DCM/Pyridine (80 mL/10 mL) was added MsCl (4.5 g, 39 mmol) under N2 at 0° C. over a period of 30 min. The reaction mixture was stirred at 25° C. for 8 hours. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was washed with brine and dried over Na2SO4. After concentration, the residue was purified by column chromatography (PE) to give crude product of 5-bromo-2-cyclopropyl-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (4.5 g, yield: 90%). 1H-NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.71 (s, 1H), 6.79 (s, 1H), 5.93 (s, 1H), 3.06 (d, J=4.8 Hz, 3H), 2.96 (s, 3H), 2.59˜2.61 (m, 1H), 1.13˜1.14 (m, 2H), 1.16˜1.20 (m, 2H). MS (M+H)+: 387/389.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue was purified by column chromatography (PE)

Sources & evidence

ORD record
ord-c40ddcacf0604b9fb6178973d38d62c7
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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