Sodium Carbonate → 4-[[4-(3,5-Dimethyl-4-isoxazolyl)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

HRID 229294Notes

Reaction equation

HRID 229294 reaction equation
CS(C1C=CC([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[C:25]3[CH2:30][C:29]([CH3:32])([CH3:31])[CH2:28][C:27]([CH3:34])([CH3:33])[CH2:26]3)[C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=CC=1)(=O)=O.BrC1C=CC(C(=C2CC(C)(C)CC(C)(C)C2)C2C=CC(O)=CC=2)=CC=1.[CH3:60][C:61]1[C:65](B(O)O)=[C:64]([CH3:69])[O:63][N:62]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C1COCC1>[CH3:60][C:61]1[C:65]([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[C:25]3[CH2:26][C:27]([CH3:33])([CH3:34])[CH2:28][C:29]([CH3:31])([CH3:32])[CH2:30]3)[C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)=[C:64]([CH3:69])[O:63][N:62]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 111557414-[[4'-(Methylsulfonyl)-4-biphenylyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenolHCID 686543984-[(4-Bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol

Product 1

HCID 577572194-[[4-(3,5-Dimethyl-4-isoxazolyl)phenyl](3,3,5,5-tetramethylcyclohexylidene)methyl]phenolYield 83%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The Suzuki protocol described for (163) was employed; A round bottom flash was charged with 4-[(4-bromophenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenol (14) (0.200 g, 0.5 mmol), PdCl2(PPh3)2 (0.035 g, 0.05 mmol), (3,5-dimethyl-4-isoxazolyl)boronic acid (0.141 g, 1.0 mmol), aqueous 2 M Na2CO3 (1.0 mL, 0.106 g, 1.0 mmol) solution, and 4:1 THF:H2O mixture (5 mL) under a nitrogen atmosphere. The reaction mixture was refluxed for 3 h. Regular work-up and purification gave 0.172 g (83%) of the title compound (235) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.30 (s, 1H), 7.29 (d, J=8.0 Hz, 2H), 7.21 (d, J=8.4 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.67 (d, J=8.4 Hz, 2H), 2.38 (s, 3H), 2.20 (s, 2H), 1.91 (br s, 4H), 1.25 (s, 2H), 0.892 (s, 6H), 0.88 (s, 6H). LCMS (APCI): m/z 416.10 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customRegular work-up and purification

Sources & evidence

ORD record
ord-358f7db3160e42008ebb9d65062cce43
Source dataset
uspto-grants-2009_07
Patent number
US07560589B2

Reaction notes

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