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

HRID 989168Notes

Reaction equation

HRID 989168 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-a5c2e55e2d2e4702883145ed28f80446
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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