Hydrochloric Acid → 3-Fluoro-4-(morpholine-4-carbonyl)phenylboronic acid

HRID 632473Notes

Reaction equation

HRID 632473 reaction equation
[B:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[C:6]([F:13])[CH:5]=1)([OH:3])[OH:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.Cl>CN(C=O)C>[F:13][C:6]1[CH:5]=[C:4]([B:1]([OH:2])[OH:3])[CH:12]=[CH:11][C:7]=1[C:8]([N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 27632014-Carboxy-3-fluorophenylboronic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 576184153-Fluoro-4-(morpholine-4-carbonyl)phenylboronic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-borono-2-fluorobenzoic acid (1.0 g, 5.43 mmol) and HATU (2.0 g, 5.43 mmol) in DMF (20.0 mL) was added morpholine (0.9 g, 10.87 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into ice cold water, acidified with 1N HCl, extracted with EtOAc (2×50 mL). The organic layer was washed with brine solution (20 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure to afford 1.2 g of crude compound as a colourless gum. Crude compound was directly used for the next step without any further purification.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe organic layer was washed with brine solution (20 mL)
  4. dry with materialdried over anhydrous Na2SO4 and solvent
  5. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-cebe5f0af8654e32bfbe31811e2ffc75
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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