Potassium Phosphate, Tribasic → HCID 57484710, compound

HRID 1802340Notes

Reaction equation

HRID 1802340 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].C1(P([CH:25]2[CH2:30][CH2:29]CCC2)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>[CH:29]1([C:2]2[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=2[O:10][CH3:11])[CH2:30][CH2:25]1

Participants

7

Reactant 3

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

Product 1

HCID 57484710HCID 57484710, 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, 300 mg, 1.41 mmol, 1.0 equiv), potassium cyclopropyl(trifluoro)borate (521 mg, 3.52 mmol, 2.5 equiv), tricyclohexylphosphine (158 mg, 0.56 mmol, 0.4 equiv), palladium(II) acetate (63.2 mg, 0.28 mmol, 0.2 equiv) and tripotassium phosphate (1046 mg, 4.93 mmol, 3.5 equiv) were suspended in toluene (15 mL) and water (0.75 mL). The reaction mixture was heated in a microwave reactor for 60 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 (3-5). ESI+MS [M+H]+ C10H11N2O: 175.1 found, 175.2 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-e9dd915f855540dcbb7e6641a100bb33
Source dataset
uspto-grants-2013_01
Patent number
US08349872B2

Reaction notes

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