Sodium cyanoborohydride → 5-Methoxy-6-(trifluoromethyl)indoline

HRID 1740803Notes

Reaction equation

HRID 1740803 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][CH:7]=[CH:6]2.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:13])[F:14])[NH:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 108225525-Methoxy-6-(trifluoromethyl)-1H-indole

Product 1

HCID 112067135-Methoxy-6-(trifluoromethyl)indolineYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The indole (D28) (67.63 g, 0.315 mol) was treated with sodium cyanoborohydride (40 g, 0.637 mol) in glacial acetic acid (500 ml) as in the method of Description 16 to afford the title indoline (67.73 g, 99%) as an off-white solid.

Sources & evidence

ORD record
ord-45620977afb4457fb66ea35d8800366f
Source dataset
uspto-grants-1999_10
Patent number
US05972937

Reaction notes

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