2-(4-Fluorophenyl)acetic acid → HCID 89924303, compound

HRID 1051868Notes

Reaction equation

HRID 1051868 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.C(=O)(O)[O-].[Na+].[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.ClCCl.O>[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([B:4]3[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)=[CH:10][CH:11]=2)=[O:31])=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 98372-(4-Fluorophenyl)acetic acidHCID 516892Sodium Bicarbonate2×HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 89924303HCID 89924303, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (200 mg) in DMF (9 mL) and dichloromethane (18 mL) was added sodium bicarbonate (153 mg), (4-fluorophenyl)acetic acid (155 mg) and HATU (521 mg). The mixture was stirred at room temperature for 4 h. Water was added, and the mixture was stirred for 30 minutes. A half-saturated solution of sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Aminophase-silica-gel chromatography gave 120 mg of the title compound.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-a932493ce0784472ae01b8b3c0a33625
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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