Dimethylformamide → 5-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

HRID 49518Notes

Reaction equation

HRID 49518 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]OS(C)(=O)=O)=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.C[CH:32]=[CH:33][CH2:34][NH2:35].[OH-].[Na+].[CH3:38]N(C=O)C>>[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][N:35]([CH2:34][CH:33]=[CH2:32])[CH3:38])=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 304472-Buten-1-amineHCID 865870136-Fluoro-5-(5-methanesulfonyloxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester

Product 1

HCID 101373155-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl esterYield 67%

Procedure

A solution of 30 mg (0.066 mmol) of 6-Fluoro-5-(5-methanesulfonyloxy-pent-1-ynyl)-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester and 0.1 ml (0.10 mmol) N-methylallylamine in 0.5 ml of DMF was stirred at 80° C. for 2 hours. The mixture was poured into 0.5 M aqueous NaOH and extracted with EtOAc. Drying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with EtOAc/MeOH/NEt3 10:1:0.1 gave 19 mg (67%) of 5-[5-(Allyl-methyl-amino)-pent-1-ynyl]-6-fluoro-2,3-dihydro-indole-1-carboxylic acid 4-chloro-phenyl ester as a light brown oil, MS: 427 (MH+, 1Cl).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialDrying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with EtOAc/MeOH/NEt3 10:1:0.1

Sources & evidence

ORD record
ord-97fa5d48d925413ea3bacb65d5d2acff
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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