5-methyl-2-(trifluoromethyl)furan-3-sulfonyl Chloride → HCID 57901600, compound

HRID 1851575Notes

Reaction equation

HRID 1851575 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].[CH3:16][C:17]1[O:21][C:20]([C:22]([F:25])([F:24])[F:23])=[C:19]([S:26](Cl)(=[O:28])=[O:27])[CH:18]=1>N1C=CC=CC=1>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH:15][S:26]([C:19]1[CH:18]=[C:17]([CH3:16])[O:21][C:20]=1[C:22]([F:25])([F:23])[F:24])(=[O:28])=[O:27]

Participants

4

Reactant 2

HCID 27798955-methyl-2-(trifluoromethyl)furan-3-sulfonyl ChlorideHCID 579017772-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine

Product 1

HCID 57901600HCID 57901600, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine (100 mg) and pyridine (3 mL) was added 5-methyl-2-trifluoromethylfuran-3-sulfonyl chloride (150 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (90 mg, yield 46%) as pale-yellow crystals. M+1=430.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dacba3127e4e478d9ad5cfd385cd46f3
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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