Cesium carbonate → HCID 53477130, compound

HRID 1878633Notes

Reaction equation

HRID 1878633 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:5]2.[C:16]1([C:22]2[CH:23]=[C:24]([NH2:28])[CH:25]=[N:26][CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH2:12]([N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:28][C:24]3[CH:25]=[N:26][CH:27]=[C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:23]=3)[CH:3]=2)[C:7]1=[O:11])[CH2:13][CH2:14][CH3:15]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 27629015-Phenylpyridin-3-amineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 67432057HCID 67432057, compound

Product 1

HCID 53477130HCID 53477130, compoundYield 55.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

5-Bromo-2-butylisoindolin-1-one (71.6 mg, 0.267 mmol), 5-phenylpyridin-3-amine (50.0 mg, 0.294 mmol) and Cs2CO3 (217.0 mg, 0.668 mmol) were added to suspension of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (X-Phos) (12.7 mg, 0.027 mmol) and palladium acetate (PdOAc2) (8.0 mg, 0.040 mmol) in toluene (2 mL). The mixture was stirred and heated in the microwave (120° C., 300 W, 60 min). Water and ethyl acetate were added. The organic layer was separated, the aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4. Purification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol) provided 2-butyl-5-(5-phenylpyridin-3-ylamino)isoindolin-1-one (53 mg, 54%). ESI-MS [M+H]+=358.1.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. customPurification by flash chromatography (dichloromethane/methanol, gradient 1-5% methanol)

Sources & evidence

ORD record
ord-6d499d031d8c4330b99d9c7f12944549
Source dataset
uspto-grants-2012_11
Patent number
US08314120B2

Reaction notes

Loading…