Pyridine-2-sulfonyl Chloride → ethyl 5-(3-methoxypropoxy)-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylate

HRID 1994836Notes

Reaction equation

HRID 1994836 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[CH3:21][O:20][CH2:19][CH2:18][CH2:17][O:16][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([NH:1][S:28]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=3)(=[O:30])=[O:29])[CH:3]=1)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2

Participants

4

Reactant 2

HCID 3787675Pyridine-2-sulfonyl ChlorideHCID 57476210ethyl 7-amino-5-(3-methoxypropoxy)-1H-indole-2-carboxylate

Product 1

HCID 57476212ethyl 5-(3-methoxypropoxy)-7-[(pyridin-2-ylsulfonyl)amino]-1H-indole-2-carboxylateYield 90.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of ethyl 7-amino-5-(3-methoxypropoxy)-1H-indole-2-carboxylate (3.00 g) and pyridine (50 mL) was added pyridine-2-sulfonyl chloride (2.0 g) at 0° C., and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated, 1N hydrochloric acid and ethyl acetate were added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and saturated brine, dried (MgSO4), and concentrated. The obtained residue was subjected to silica gel column chromatography, and eluted with hexane-ethyl acetate (2:1-1:1, volume ratio) to give the title compound (4.02 g, yield 90%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give colorless prism crystals. melting point 126-127° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1N hydrochloric acid and ethyl acetate were added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed successively with water and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washeluted with hexane-ethyl acetate (2:1-1:1, volume ratio)

Sources & evidence

ORD record
ord-52f977e7be164144913c2e78b89900d6
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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