Sodium Bicarbonate → 1,1,1-Trifluoro-4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-(((2-methylquinolin-5-yl)amino)methyl)pentan-2-ol

HRID 2220241Notes

Reaction equation

HRID 2220241 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:33])([CH3:32])[CH2:12][C:13]([OH:31])([C:27]([F:30])([F:29])[F:28])[CH:14]=[N:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][C:20]([CH3:26])=[N:21]3)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:33])([CH3:32])[CH2:12][C:13]([OH:31])([C:27]([F:28])([F:30])[F:29])[CH2:14][NH:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][C:20]([CH3:26])=[N:21]3)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 4311764Sodium borohydrideHCID 441850445-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-2-methylquinoline

Product 1

HCID 116267821,1,1-Trifluoro-4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-4-methyl-2-(((2-methylquinolin-5-yl)amino)methyl)pentan-2-olYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-[4-(5-Fluoro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentylidenamino]-2-methylquinoline (266 mg, 0.58 mmol) and sodium bicarbonate (250 mg) in methanol (15 ml) are stirred for 15 minutes at room temperature. Sodium borohydride (152 mg, 4 mmol) is added thereto in 4 portions over 24 hours. After the reaction is completed (TLC monitoring), the batch is mixed with saturated NaHCO3 solution (10 ml) and concentrated by evaporation. The residue is taken up in ethyl acetate (30 ml) and water (20 ml), and the phases are separated. The aqueous phase is extracted with ethyl acetate. The combined organic phases are dried (Na2SO4) and concentrated by evaporation. Column chromatography on silica gel with hexane-ethyl acetate yields 200 mg of the product.

Workup

  1. concentrationconcentrated by evaporation
  2. customwater (20 ml), and the phases are separated
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried (Na2SO4)
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-998c8048a0d240ae9dc775d991fb0725
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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