Triethylamine → (S)-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanol

HRID 2059888Notes

Reaction equation

HRID 2059888 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10](Cl)(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][C@H:16]1[CH2:24][OH:25].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][C@H:16]2[CH2:24][OH:25])(=[O:12])=[O:11])=[C:5]([CH3:14])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6951186(S)-(+)-2-IndolinemethanolHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 57989609(S)-(1-(4-Methoxy-2,6-dimethylphenylsulfonyl)indolin-2-yl)methanolYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4-Methoxy-2,6-dimethylbenzenesulfonic acid chloride (3.83 mmol, 1.0 eq) in DCM (5 ml) was added dropwise to a cooled (0° C.) solution of (S)-indolin-2-ylmethanol (4.60 mmol, 1.2 eq) and triethylamine (2.5 eq) in DCM (20 ml) and the mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with DCM and washed with water and saturated sodium chloride solution. It was dried over sodium sulfate and concentrated to small volume under vacuum. The crude product was processed by column chromatography. Yield: 72%

Workup

  1. washwashed with water and saturated sodium chloride solution
  2. dry with materialIt was dried over sodium sulfate
  3. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-df02078f8a884d8782ecfc7e521cea77
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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