Ethyl Acetate → HCID 67326675, compound

HRID 1257077Notes

Reaction equation

HRID 1257077 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[CH:13][C:14]2[CH2:18][O:17][B:16]([OH:19])[C:15]=2[CH:20]=1)[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].[Cl:27]C1C=C(C=CC=1F)C#N.CCOC(C)=O>CS(C)=O>[Cl:27][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]1[CH:12]=[CH:13][C:14]2[CH2:18][O:17][B:16]([OH:19])[C:15]=2[CH:20]=1)[C:5]#[N:6]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1455253-Chloro-4-fluorobenzonitrileHCID 67326361HCID 67326361, compound

Product 1

HCID 67326675HCID 67326675, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3H-benzo[c][1,2]oxaborole-1,6-diol (5) (300 mg, 2 mmol) in DMSO (30 mL) were added K2CO3 (828 mg, 6 mmol) and 3-chloro-4-fluoro-benzonitrile (933 mg, 6 mmol). The reaction was heated at 90° C. for 7 hours. After the cooling of reaction solution, EtOAc (50 mL) was added. The organic layer was washed with water (5×50 mL). The organic layer was evaporated under vacuum. The residue was purified by reverse phase chromatography to afford 3-chloro-4-(1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-benzonitrile (6) 190 mg in 33.3% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.24 (s, 1 H), 8.22 (s, 1 H), 7.77 (d, J=7.81 Hz, 1 H), 7.50 (d, J=8.20 Hz, 1 H), 7.34 (s, 1 H), 7.28 (d, J=8.20 Hz, 1 H), 7.01 (d, J=8.59 Hz, 1 H), 4.99 (s, 2 H). ESMS (m/z): 284 (M−H)−. HPLC: 96.41% (220 nm), 96.0% (maxplot).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water (5×50 mL)
  3. customThe organic layer was evaporated under vacuum
  4. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-56e190adf3684b98968c5f4a35288dca
Source dataset
uspto-grants-2013_06
Patent number
US08461336B2

Reaction notes

Loading…