Methanol → HCID 89907880, compound

HRID 526692Notes

Reaction equation

HRID 526692 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[N:10][C:11]([CH3:17])=[C:12]([CH:16]=2)[C:13](O)=[O:14])=[CH:4][CH:3]=1.B.CO>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[C:12]([CH2:13][OH:14])[C:11]([CH3:17])=[N:10][C:9]=2[C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 89906543HCID 89906543, compound

Product 1

HCID 89907880HCID 89907880, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.6 g of 5-(4-Chloro-phenyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-nicotinic acid in 38 ml of THF, were added dropwise 12 ml of a 1M solution of borane in THF at room temperature. Then, the reaction mixture was heated to reflux for 5 h. The reaction mixture was cooled to room temperature and 20 ml of methanol were carefully added. The solvents were removed under reduced pressure and the residue was dissolved in ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, saturated sodium chloride solution and saturated sodium hydrogen carbonate solution. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. the residue was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate. The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 1.2 g.

Workup

  1. temperatureThen, the reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. customThe solvents were removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe organic layer was washed with 1 M hydrochloric acid, saturated sodium chloride solution and saturated sodium hydrogen carbonate solution
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified by chromatography on silica gel eluting with a gradient of n-heptane/ethyl acetate
  10. additionThe fractions containing the product
  11. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e9bc17037c84f5b9e0aa8cf6f1b4db3
Source dataset
uspto-grants-2016_05
Patent number
US09346757B2

Reaction notes

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