Sodium Carbonate → HCID 11485600, compound

HRID 2100172Notes

Reaction equation

HRID 2100172 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:21]2[CH2:26][C:25](C)([CH3:27])[CH2:24][C:23](C)(C)[CH2:22]2)[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](OC)=O)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.CC1[C:36](B(O)O)=[C:35](C)[O:34][N:33]=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.C1COCC1.O>[C:21]1(=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([CH3:17])=[N:33][O:34][C:35]=3[CH3:36])=[CH:11][CH:10]=2)[C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH2:26][CH2:25][CH2:27][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 68654562Methyl 3-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}propanoate

Product 1

HCID 11485600HCID 11485600, compoundYield 114.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

The procedure described for 202 was followed. A round-bottomed flask was charged with 4-[(4-bromophenyl)(cycloheptylidene)methyl]phenol (9) (0.100 g, 0.28 mmol), PdCl2(PPh3)2, (0.020 g, 0.028 mmol), (3,5-dimethyl-4-isoxazolyl)boronic acid (0.079 g, 0.56 mmol), Na2CO3 (0.060 g, 0.56 mmol), and THF/H2O (5 mL, 4:1). The reaction mixture was refluxed for 10 h. Standard workup and purification by flash silica gel chromatography provided 0.120 g (78%) of the title compound 206 as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 9.28 (s, 1H), 7.28 (d, J=6.00 Hz, 2H), 7.18 (d, J=6.0 Hz, 2H), 6.94 (d, J=6.6 Hz, 2H), 6.67 (d, J=6.3 Hz, 2H), 2.37 (s, 3H), 2.23-2.22 (br, m, s, 4H), 1.52 (br s, 8H). LCMS (ESI): m/z 372 (M−H)−.

Workup

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. customStandard workup and purification by flash silica gel chromatography

Sources & evidence

ORD record
ord-2a506124b6804ae09305c89030eaf32a
Source dataset
uspto-grants-2009_08
Patent number
US07569601B2

Reaction notes

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