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

HRID 1845298노트

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HRID 1845298 반응식
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

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 58187949Methyl 3-bromo-5-(hydroxy(thiazol-2-yl)methyl)benzoate

생성물 1

HCID 58188318Methyl 5-(hydroxy(thiazol-2-yl)methyl)-4'-methylbiphenyl-3-carboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-c08a7ae3805540ca91b93ac600ed904a
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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