Sodium hydride → HCID 57039673, compound

HRID 1067819Notes

Reaction equation

HRID 1067819 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:7]2.[H-].[Na+].ICCCN[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O>[C:28]([O:27][C:26]([CH:6]([NH2:7])[CH2:5][CH2:4][N:7]1[C:8]2[C:4](=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:11]=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:32])([CH3:29])([CH3:30])[CH3:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11231463tert-butyl N-(3-iodopropyl)carbamateHCID 14859085Ethyl 4-(trifluoromethyl)-1H-indole-2-carboxylate

Product 1

HCID 57039673HCID 57039673, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out in a manner similar to Reference Example 5 (25) except for using 2.60 g (10.11 mmol) of ethyl 4-trifluoromethyl-2-indolecarboxylate, 0.445 g (11.12 mmol) of 60% sodium hydride, 4.32 g (15.17 mmol) of tert-butyl N-(3-iodopropyl)-carbamate and 100 ml of dimethylformamide. Ethyl 1-(3-tert-butoxycarbonyl-aminopropyl)-4-trifluoromethyl-2-indolecarboxylate was thus obtained in an amount of 2.81 g (67.1%).

Sources & evidence

ORD record
ord-451951a7a9934900a976c5286799b981
Source dataset
uspto-grants-2001_06
Patent number
US06248772B1

Reaction notes

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