Potassium Carbonate → HCID 57459629, compound

HRID 1428508Notes

Reaction equation

HRID 1428508 reaction equation
I[C:2]1[C:3]2[N:4]([C:9]([CH2:12][CH:13]3[CH2:15][CH2:14]3)=[N:10][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:16](B(O)O)[CH3:17].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:16]([C:2]1[C:3]2[N:4]([C:9]([CH2:12][CH:13]3[CH2:15][CH2:14]3)=[N:10][N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8])[CH3:17]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 521157Ethylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57459624HCID 57459624, compound

Product 1

HCID 57459629HCID 57459629, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To a mixture of intermediate D70 (0.6 g, 1.8 mmol) in toluene (14 ml) under a nitrogen atmosphere were added ethylboronic acid (0.665 g, 9 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; X-Phos (0.171 g, 0.36 mmol), palladium(II) acetate (0.04 g, 0.18 mmol) and K2CO3 (0.745 g, 5.396 mmol). The reaction mixture was heated at 100° C. overnight. After cooling, the mixture was diluted with EtOAc and washed with water. The organic layer was separated and concentrated in vacuo. The residue was purified by column chromatography (silica gel; DCM/EtOAc from 100/0 to 20/80 as eluent). The desired fractions were collected and concentrated in vacuo to give a residue that was purified by HPLC to yield intermediate D81 (0.053 g, 12.6%).

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel; DCM/EtOAc from 100/0 to 20/80 as eluent)
  6. customThe desired fractions were collected
  7. concentrationconcentrated in vacuo
  8. customto give a residue that
  9. customwas purified by HPLC
  10. customto yield intermediate D81 (0.053 g, 12.6%)

Sources & evidence

ORD record
ord-9ba72b3666da463e86517f87b139a74c
Source dataset
uspto-grants-2015_01
Patent number
US08937060B2

Reaction notes

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