Difluoromethanesulphonyl chloride → 2-(4-Bromophenyl)-5-cyclopropyl-6-{[(difluoromethyl)sulfonyl]amino}-N-methyl-2H-indazole-3-carboxamide

HRID 1037532Notes

Reaction equation

HRID 1037532 reaction equation
[NH2:1][C:2]1[C:3]([CH:22]2[CH2:24][CH2:23]2)=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[C:6]=2[C:18]([NH:20][CH3:21])=[O:19].[F:25][CH:26]([F:31])[S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[Br:17][C:14]1[CH:13]=[CH:12][C:11]([N:7]2[C:6]([C:18]([NH:20][CH3:21])=[O:19])=[C:5]3[C:9]([CH:10]=[C:2]([NH:1][S:27]([CH:26]([F:31])[F:25])(=[O:29])=[O:28])[C:3]([CH:22]4[CH2:24][CH2:23]4)=[CH:4]3)=[N:8]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 73932Difluoromethanesulphonyl chlorideHCID 675127246-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide

Product 1

HCID 675174732-(4-Bromophenyl)-5-cyclopropyl-6-{[(difluoromethyl)sulfonyl]amino}-N-methyl-2H-indazole-3-carboxamideYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound (47) was prepared by the following method: To a suspension of 6-amino-2-(4-bromophenyl)-5-cyclopropyl-N-methyl-2H-indazole-3-carboxamide (20 mg, 0.052 mmol) in neat pyridine (1 mL) at 0° C. was added difluoromethanesulfonyl chloride (60 μL). After 3 d, the reaction was quenched with saturated aqueous ammonium chloride (1 mL) and then extracted with ethyl acetate (3×2 mL). The combined organics were washed with 1M aqueous citric acid (2 mL), brine (2 mL) then dried (MgSO4) and concentrated to dryness to afford crude 2-(4-Bromophenyl)-5-cyclopropyl-6-{[(difluoromethyl)sulfonyl]amino}-N-methyl-2H-indazole-3-carboxamide (18 mg, 69%) which was used without further purification.

Workup

  1. customCompound (47) was prepared by the following method
  2. customthe reaction was quenched with saturated aqueous ammonium chloride (1 mL)
  3. extractionextracted with ethyl acetate (3×2 mL)
  4. washThe combined organics were washed with 1M aqueous citric acid (2 mL), brine (2 mL)
  5. dry with materialthen dried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a40bf32baa3140d085e10be6badc9e9e
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

Loading…