Potassium Carbonate → Methyl 5-(hydroxy(thiazol-2-yl)methyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845298Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]([OH:18])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].B(O)(O)[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.O1CCOCC1>[OH:18][CH:12]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)[C:10]1[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=[C:2]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[CH:11]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a mixture of methyl 3-bromo-5-(hydroxy(thiazol-2-yl)methyl)benzoate (320 mg, 0.98 mmol), p-tolylboronic acid (0.16 g, 1.2 mmol), potassium carbonate (0.20 g, 1.5 mmol), 1,4-dioxane (5 mL), and water (0.5 mL, 0.03 mol) under argon was added tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.052 mmol). The reaction mixture was heated at 95° C. for 8 h. After cooling, the mixture was treated with water (15 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were dried (MgSO4) and concentrated. The residue was purified by flash chromatography to afford the title compound.

Workup

temperatureAfter cooling
extractionextracted with EtOAc (20 mL×3)
dry with materialThe combined organic layers were dried (MgSO4)
concentrationconcentrated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-c08a7ae3805540ca91b93ac600ed904a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946439B2

Reaction notes

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