Potassium Phosphate, Tribasic → HCID 66665431, compound

HRID 872360Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:28][CH3:29])[C:5]2[N:6]([C:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]4([NH2:21])[CH2:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[C:30]([O:34][C:35]([N:37]1[CH:41]=[C:40](B(O)O)[CH:39]=[N:38]1)=[O:36])([CH3:33])([CH3:32])[CH3:31].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCO.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:30]([O:34][C:35]([N:37]1[CH:41]=[C:40]([C:2]2[CH:3]=[C:4]([O:28][CH3:29])[C:5]3[N:6]([C:8]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:9]([C:11]4[CH:16]=[CH:15][C:14]([C:17]5([NH2:21])[CH2:18][CH2:19][CH2:20]5)=[CH:13][CH:12]=4)[N:10]=3)[CH:7]=2)[CH:39]=[N:38]1)=[O:36])([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-[4-(6-bromo-8-methoxy-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (120 mg), [1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl]boronic acid (170 mg) and potassium phosphate (170 mg) in toluene (0.9 mL), EtOH (1.86 mL) and water (0.93 mL) was placed under argon and bis(tri-tert-butyl phosphine)palladium(0) (13.7 mg) was added. The mixture was heated at 120° C. under microwave irradiation for 30 minutes. On cooling the mixture was partitioned between DCM and water and the phases separated. The organic portion was concentrated in vacuo to give the crude title compound which was used in the next step without further purification.

Workup

temperatureOn cooling the mixture
customwas partitioned between DCM and water
customthe phases separated
concentrationThe organic portion was concentrated in vacuo

Sources & evidence

ORD record: ord-b96be80b46a04402b6052de98ba0c3c7
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975265B2

Reaction notes

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