Phenylboronic Acid → HCID 59540290, compound

HRID 404656Notes

Reaction equation

HRID 404656 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]1([F:17])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.O.O=[CH:20][C:21]([OH:23])=[O:22]>C(Cl)Cl>[F:10][C:11]1([F:17])[CH2:16][CH2:15][N:14]([CH:20]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:21]([OH:23])=[O:22])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 27583524,4-DifluoropiperidineHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 59540290HCID 59540290, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of phenylboronic acid (400 mg, 3.28 mmol), 4,4-difluoropiperidine (397 mg, 3.28 mmol) and 2-oxoacetic acid hydrate (302 mg, 3.28 mmol) in DCM (30 ml) was stirred at room temperature overnight. DCM was evaporated and crude was purified by flash-chromatography (DCM/MeOH=8/2) to obtain the title compound (512 mg, 61.1% yield) as a white solid.

Workup

  1. customDCM was evaporated
  2. customcrude was purified by flash-chromatography (DCM/MeOH=8/2)

Sources & evidence

ORD record
ord-6b07a76076e54e6c8d11f56304716fda
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

Loading…