Cesium carbonate → HCID 58110358, 화합물

HRID 238277

반응식

HRID 238277 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8](Br)[S:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].C(OC([N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1)=O)(C)(C)C>COCCOC.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:27]2[CH:28]=[N:24][NH:25][CH:26]=2)[S:7][CH:6]=1)=[O:4]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 45873035Methyl 5-bromothiophene-3-carboxylate

생성물 1

HCID 58110358HCID 58110358, 화합물수율 53.5%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
110 °C

실험 절차

5-Bromo-thiophene-3-carboxylic acid methyl ester (6 g, 27 mmol) was dissolved in a mixture of DME (75 mL), IMS (25 mL) and water (12.5 mL). Caesium carbonate (13.2 g, 40 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazole-1-carboxylic acid tert-butyl ester (9.2 g, 31 mmol) were added and the mixture stirred under argon. Palladium tetrakis-(triphenylphosphine) (3.1 g, 2.7 mmol) was then added and the mixture heated at 110° C. for 6 hours. The mixture was allowed to cool to room temperature and then diluted with water. The product was extracted into DCM and washed with brine, then dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was triturated with diethyl ether to give the title compound as a pale yellow solid (3.01 g). LCMS m/z 209.1 [M+H]+. R.T.=3.72 min (Analytical Method 4). 1H NMR (400 MHz, d6-DMSO): δ 8.2 (s, 1H), 8.15 (s, 1H), 7.85 (s, 1H), 7.5 (s, 1H), 3.8 (s, 3H).

후처리

  1. temperatureto cool to room temperature
  2. extractionThe product was extracted into DCM
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed by evaporation under vacuum
  7. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-7cb3435494504c13b0bb5791727fe208
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642621B2

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