2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 66920433, compound

HRID 1510088Notes

Reaction equation

HRID 1510088 reaction equation
[Cl-].[CH3:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Zn+].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]([C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH2:42][CH2:43][O:44][CH3:45])[C:27]=2Cl)=[O:25])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH2:20][N:21]([C:24]([C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH2:42][CH2:43][O:44][CH3:45])[C:27]=2[CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[CH3:2])=[O:25])[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 66920466HCID 66920466, compoundHCID 178424246HCID 178424246, compound

Product 1

HCID 66920433HCID 66920433, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A solution of 2-methylbenzylzinc chloride (1.95 ml, 973 μmol, 0.5 M in THF) was added dropwise at −78° C. to a solution of B-OM-9-BBN (0.97 ml, 973 μmol, 1 M in hexane). The cooling bath was removed and the mixture was stirred at room temperature for 30 min. DMF (2 ml) was added, followed by the compound of step 5 (50 mg, 97.3 μmol), palladium(II) acetate (2.18 mg, 9.73 μmol) and S-PHOS (7.99 mg, 19.5 μmol). The reaction mixture was heated to 100° C. and stirred for 4 h. The mixture was diluted with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by preparative HPLC. The eluate was lyophilized overnight to give 14 mg of the title compound.

Workup

  1. customThe cooling bath was removed
  2. additionDMF (2 ml) was added
  3. temperatureThe reaction mixture was heated to 100° C.
  4. stirringstirred for 4 h
  5. extractionextracted with EA
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe residue was purified by preparative HPLC
  11. waitThe eluate was lyophilized overnight

Sources & evidence

ORD record
ord-374f24a1536d4779ac2f220bb5ee315f
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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