Sodium Bicarbonate → HCID 59448381、化合物

HRID 1925025ノート

反応式

HRID 1925025 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 59448381HCID 59448381、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-be916498b32240a1a31a23e5717724ef
出典データセット
uspto-grants-2012_05
特許番号
US08178549B2

反応ノート

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