4-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine → HCID 68226428, compound

HRID 520579Notes

Reaction equation

HRID 520579 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([NH:23][C:24]([C:26]4[O:27][CH:28]=[CH:29][CH:30]=4)=[O:25])[CH:15]=[C:16]([Sn](C)(C)C)[CH:17]=3)[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:32]1[CH:37]=[CH:36][N:35]=[C:34]2[N:38]([S:41]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)(=[O:43])=[O:42])[CH:39]=[CH:40][C:33]=12>CN(C=O)C>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([NH:23][C:24]([C:26]4[O:27][CH:28]=[CH:29][CH:30]=4)=[O:25])[CH:15]=[C:16]([C:32]4[CH:37]=[CH:36][N:35]=[C:34]5[N:38]([S:41]([C:44]6[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=6)(=[O:42])=[O:43])[CH:39]=[CH:40][C:33]=45)[CH:17]=3)[CH:12]=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridineHCID 66691550HCID 66691550, compound

Product 1

HCID 68226428HCID 68226428, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-2-furancarboxamide (216 mg) and 4-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (182 mg) with Solvias catalyst (11 mg) in DMF (3 ml) was heated at 120° C. for 20 min in the microwave. The solvent was evaporated and the residue was purified on 20 g silica cartridge using ether and then 10% ethyl acetate:ether. The appropriate fractions were evaporated to dryness and triturated with ether to give the title compound, 90 mg as an off-white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified on 20 g silica cartridge
  3. customThe appropriate fractions were evaporated to dryness
  4. customtriturated with ether

Sources & evidence

ORD record
ord-e6d152184430422b82ce4b28036e56ef
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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