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

HRID 1603756Notes

Reaction equation

HRID 1603756 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 (D10) (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 1 to afford the title indoline (67.73 g, 99%) as an off-white solid.

Sources & evidence

ORD record
ord-326fdfb2c6f6498ca80c2b734f0f3b3d
Source dataset
uspto-grants-1999_11
Patent number
US05990133

Reaction notes

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