Sodium borohydride → 1-(Quinolin-5-ylamino)-3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-(trifluoromethyl)propan-2-ol

HRID 2215422Notes

Reaction equation

HRID 2215422 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([N:11]=[CH:12][C:13]([C:28]([F:31])([F:30])[F:29])([OH:27])[CH2:14][C:15]3([C:18]4[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=4[O:25][CH3:26])[CH2:17][CH2:16]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].CCCCCC.C(OCC)(=O)C>CO.O1CCCC1>[N:1]1[C:10]2[C:5](=[C:6]([NH:11][CH2:12][C:13]([C:28]([F:31])([F:29])[F:30])([OH:27])[CH2:14][C:15]3([C:18]4[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=4[O:25][CH3:26])[CH2:16][CH2:17]3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226206Ethyl acetate hexaneHCID 21948889HCID 21948889, compound

Product 1

HCID 219488751-(Quinolin-5-ylamino)-3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-(trifluoromethyl)propan-2-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

810 mg (1.87 mmol) of 1-(quinolin-5-ylimino)-3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-(trifluoromethyl)propan-2-ol is reacted with 288 mg (7.61 mmol) of sodium borohydride in 6.0 ml of methanol and 3.0 ml of tetrahydrofuran as in Example 1. After chromatography on silica gel with hexane-ethyl acetate (0–100%), 660 mg (81% of theory) of the product is obtained.

Sources & evidence

ORD record
ord-0f4151e6e5d34db585fa1eb0320ccafd
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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