Potassium Carbonate → HCID 66788346, compound

HRID 587644Notes

Reaction equation

HRID 587644 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.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

8

Reactant 4

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2×HCID 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 D70 (0.6 g, 1.8 mmol) in toluene (15 ml) under a nitrogen atmosphere were added methylboronic acid (0.538 g, 9 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine; S-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 yield intermediate D71 (0.312 g, 78%) as a cream solid.

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 yield intermediate D71 (0.312 g, 78%) as a cream solid

Sources & evidence

ORD record
ord-2092c433528b459088e20b56aac656d8
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

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