Sodium Bicarbonate → HCID 59448381, 화합물

HRID 1925025노트

반응식

HRID 1925025 반응식
Br[C:2]1[CH:3]=[N:4][S:5][CH:6]=1.[CH3:7][O:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12](B(O)O)=[CH:11][N:10]=1.C([O-])(O)=O.[Na+]>COCCOC.O>[S:5]1[CH:6]=[C:2]([C:12]2[C:13]([O:15][CH3:16])=[N:14][C:9]([O:8][CH3:7])=[N:10][CH:11]=2)[CH:3]=[N:4]1

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 52003584-Bromo-isothiazole

생성물 1

HCID 59448381HCID 59448381, 화합물

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

4-bromoisothiazole (commercially available from Aurora, 500 mg, 3.05 mmol) was dissolved in degassed 1,2-Dimethoxyethane (DME) (5 ml). Pd(Ph3)4 (176 mg, 0.152 mmol) was added thereto. The reaction mixture was stirred at room temperature for 15 min. [2,4-bis(methyloxy)-5-pyrimidinyl]boronic acid (commercially available from Aldrich, 1178 mg, 6.40 mmol) and 5 mL of degassed 1M/H2O solution of NaHCO3 were added to the reaction mixture under N2 atm. After 2 h 30 min stirring at 90° C. the mixture was diluted with water and extracted with DCM. The collected organic phases were evaporated. The residue was purified by flash chromatography eluting with cyclohexane/EtOAc 5:1. 686 mg of the title compound were isolated as a yellow solid.

후처리

  1. additionwere added to the reaction mixture under N2 atm
  2. extractionextracted with DCM
  3. customThe collected organic phases were evaporated
  4. customThe residue was purified by flash chromatography
  5. washeluting with cyclohexane/EtOAc 5:1

출처 및 근거

ORD 기록
ord-be916498b32240a1a31a23e5717724ef
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178549B2

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