Methylamine → HCID 21936322, compound

HRID 2374751Notes

Reaction equation

HRID 2374751 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:19][NH2:20].S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>C1COCC1>[CH3:19][NH:20][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:18])([F:17])[F:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 21936322HCID 21936322, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Intermediate D2 (4.57 g, 1 eq), methylamine (9.15 mL of a 2M solution in THF) and anhydrous magnesium sulphate (4.41 g, 2 eq) was stirred at room temperature for 16 h, filtered and the solid washed thoroughly with ethyl acetate. The combined filtrates were evaporated to a solid which was suspended in ethanol (90 mL) and sodium borohydride (1.01 g, 1.5 eq) added portionwise. The mixture stirred at room temperature for 3 h and the solvent removed in vacuo and the residue partitioned between dichloromethane and water. The organic layer was washed with brine, dried and evaporated to give the title compound as a white solid. 1H-NMR (CDCl3) δ 7.68 (4H, m), 7.56-7.58 (2H, m), 7.43-7.45 (2H, m), 3.83 (2H, s), 2.50 (3H, s); MS(APCI+) found (M+1)=266, C15H14F3N requires 265.

Workup

  1. filtrationfiltered
  2. washthe solid washed thoroughly with ethyl acetate
  3. customThe combined filtrates were evaporated to a solid which
  4. stirringThe mixture stirred at room temperature for 3 h
  5. customthe solvent removed in vacuo
  6. customthe residue partitioned between dichloromethane and water
  7. washThe organic layer was washed with brine
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-d808631bab1e4e1185223c55539378f3
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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