Potassium Carbonate → HCID 66788346, compound

HRID 587651Notes

Reaction equation

HRID 587651 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].[CH3:16]B(O)O.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>[CH3:16][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]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 57459624HCID 57459624, compound

Product 1

HCID 66788346HCID 66788346, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To a mixture of intermediate D70 (1 g, 3 mmol) in toluene (25 ml) under a nitrogen atmosphere were added methylboronic acid (0.897 g, 15 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; X-Phos (0.286 g, 0.6 mmol), palladium(II) acetate (0.067 g, 0.3 mmol) and K2CO3 (1.243 g, 9 mmol). The reaction mixture was heated at 100° C. for two days. 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 0/100 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D98 (0.365 g, 55%).

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 0/100 as eluent)
  6. customThe desired fractions were collected
  7. concentrationconcentrated in vacuo
  8. customto yield intermediate D98 (0.365 g, 55%)

Sources & evidence

ORD record
ord-31b498465b214706a472c85108d0fcb2
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

Loading…