Potassium Phosphate, Tribasic → HCID 57484708, compound

HRID 1802339Notes

Reaction equation

HRID 1802339 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[B-](F)(F)(F)[CH:13]=[CH2:14].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][O:10][C:3]1[CH:4]=[CH:5][C:6]([C:8]#[N:9])=[N:7][C:2]=1[CH:13]=[CH2:14]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 23679353Potassium vinyltrifluoroborateHCID 574847096-Bromo-5-methoxy-2-pyridinecarbonitrile

Product 1

HCID 57484708HCID 57484708, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

In a microwave vial, 6-bromo-5-methoxypyridine-2-carbonitrile (3-2, 200 mg, 0.94 mmol, 1.0 equiv), potassium trifluoro(vinyl)borate (314 mg, 2.35 mmol, 2.5 equiv), tricyclohexylphosphine (52.7 mg, 0.19 mmol, 0.2 equiv), palladium(II) acetate (21.1 mg, 0.09 mmol, 0.1 equiv), and tripotassium phosphate (697 mg, 3.29 mmol, 3.5 equiv) were suspended in toluene (10 mL) and water (0.5 mL). The reaction mixture was heated in a microwave reactor for 20 minutes at 130° C. and then filtered, rinsing with EtOAc. The filtrate was concentrated and the residue purified by normal phase column chromatography (10-35% EtOAc in hexanes) to afford the product (3-3). ESI+MS [M+H]+ C9H9N2O: 161.0 found, 161.1 required.

Workup

  1. filtrationfiltered
  2. washrinsing with EtOAc
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by normal phase column chromatography (10-35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1d9f95c5c0bb4a2ab6660ddf2f3e967f
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

Loading…