Diethyl Ether → 6-Fluoro-5-(5-methanesulfonyloxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

HRID 49517Notes

Reaction equation

HRID 49517 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][OH:26])=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38].CCOCC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][O:26][S:37]([CH3:36])(=[O:39])=[O:38])=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 695151246-Fluoro-5-(5-hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

Product 1

HCID 865870136-Fluoro-5-(5-methanesulfonyloxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl esterYield 62.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 120 mg (0.321 mmol) 6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester and 0.164 ml (0.96 mmol) N-ethyldiisopropylamine in 2 ml CH2Cl2 was treated with 0.03 ml (0.385 mmol) of methanesulfonyl chloride and stirred at room temperature for 1 hour. The mixture was poured into Et2O and washed with 0.5 M HCl. Drying of the organic layer with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2 gave 91 mg (61%) of 6-Fluoro-5-(5-methanesulfonyloxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as a colorless oil, MS: 452 (MH+, 1Cl).

Workup

  1. washwashed with 0.5 M HCl
  2. dry with materialDrying of the organic layer with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2

Sources & evidence

ORD record
ord-5c8dd594d8e04e94b2702a27024d25a9
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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