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

HRID 49516Notes

Reaction equation

HRID 49516 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][C:3]=1[C:11]#[C:12][CH2:13][CH2:14][CH2:15][OH:16].C(N(C(C)C)C(C)C)C.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)=[O:28].O>C(Cl)Cl>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([O:29][C:27]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([C:11]#[C:12][CH2:13][CH2:14][CH2:15][OH:16])=[C:2]([F:1])[CH:10]=3)[CH2:6][CH2:7]2)=[O:28])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 219666155-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol

Product 1

HCID 695151246-Fluoro-5-(5-hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl esterYield 74.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 99 mg (0.45 mmol) 5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol and 0.155 ml (0.90 mmol) N-Ethyldiisopropylamine in 2 ml CH2Cl2 was treated with 0.125 ml (0.90 mmol) 4-chlorophenyl chloroformate and stirred at room temperature during 1 hour. The mixture was poured into water, extracted with EtOAc and the combined organic layers were dried with MgSO4. Evaporation of the solvent, chromatography on silica gel with CH2Cl2/MeOH 49:1 gave 125 mg (74%) of 6-Fluoro-5-(5-hydroxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as a viscous light yellow oil, MS: 374 (MH+, 1Cl).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe combined organic layers were dried with MgSO4
  3. customEvaporation of the solvent, chromatography on silica gel with CH2Cl2/MeOH 49:1

Sources & evidence

ORD record
ord-e2ae7ee208414766bb56c59d43ca13d5
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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