2-Thiophenesulfonyl chloride → HCID 57901854, compound

HRID 1851374Notes

Reaction equation

HRID 1851374 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:12][O:13][CH3:14])[C:3]=1[C:15]1[S:16][CH:17]=[CH:18][N:19]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[Cl:1][C:2]1[C:10]2[C:5](=[C:6]([NH:11][S:25]([C:21]3[S:20][CH:24]=[CH:23][CH:22]=3)(=[O:27])=[O:26])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:12][O:13][CH3:14])[C:3]=1[C:15]1[S:16][CH:17]=[CH:18][N:19]=1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 57901783HCID 57901783, compound

Product 1

HCID 57901854HCID 57901854, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 3-chloro-1-(methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indole-7-amine (0.25 g) and pyridine (8 mL) was added thiophene-2-sulfonyl chloride (0.19 g) at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (0.36 g, yield 96%) was obtained as yellow crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). melting point 128-129° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition10% aqueous citric acid solution 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-b3a2c31ccfaf4044932d8aa1924337f5
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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