5-Chloro-2-methoxybenzene-1-sulfonyl chloride → HCID 68434888, compound

HRID 2235124Notes

Reaction equation

HRID 2235124 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:25][CH3:26])=[C:19]([S:21](Cl)(=[O:23])=[O:22])[CH:20]=1>ClCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][N:11]2[S:21]([C:19]2[CH:20]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]=2[O:25][CH3:26])(=[O:22])=[O:23])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 16244446Methyl indoline-6-carboxylate

Product 1

HCID 68434888HCID 68434888, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (1.34 g, 7.6 mmol) in dichloromethane (66 ml) and pyridine (1.6 ml) was treated with 5-chloro-2-methoxy-benzenesulfonyl chloride (1.83 g, 7.6 mmol, 1 equiv.). The mixture was stirred at room temperature overnight, then diluted with dichloromethane and washed with water. The organic phase was dried with Na2SO4 and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), yielding 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester, 2.2 g (77% yield). MS (ISP): m/e=382.1 (M+H+.), δH (300 MHz; CDCl3) 7.99 (1H, d), 7.93 (1H, s), 7.61 (1H, d), 7.37 (1H, dd), 7.11 (1H, d), 6.77 (1H, d), 4.04 (2H, t), 3.83 (3H, s), 3.56 (3H, s), 3.02 (2H, t).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried with Na2SO4
  3. customevaporated
  4. customThe residue was purified by flash chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-4c145aaf750b44ba950f3fab786a6b4e
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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