Sodium Bicarbonate → 3-Bromo-6-pyridin-3-ylpyrazolo[1,5-a]pyrimidine

HRID 1255858ノート

反応式

HRID 1255858 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[Br:10][C:11]1[CH:12]=[N:13][N:14]2[CH:19]=[C:18](Br)[CH:17]=[N:16][C:15]=12.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:10][C:11]1[CH:12]=[N:13][N:14]2[CH:19]=[C:18]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:17]=[N:16][C:15]=12

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 27343783-Pyridinylboronic acidHCID 122032093,6-Dibromopyrazolo(1,5-a)pyrimidine

生成物 1

HCID 687770603-Bromo-6-pyridin-3-ylpyrazolo[1,5-a]pyrimidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

A solution of 3-pyridyl boronic acid (1.33 g, 10.8 mmol) and 3,6-dibromopyrazolo[1,5-a]pyrimidine (3.0 g, 10.8 mmol) in DMF (300 mL) and 1M aqueous sodium bicarbonate (22 mL, 22 mmol) was degassed with nitrogen and treated with palladium tetrakistriphenylphosphine (0.63 g, 0.54 mmol) and heated to 85° C. for 16 hours. The reaction was cooled to room temperature and partitioned between water/methylene chloride. The organics were washed with water and brine, dried over sodium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (1-5% methanol/methylene chloride) gave 3-bromo-6-pyridin-3-ylpyrazolo[1,5-a]pyrimidine. LC-MS EIMS: m/z 275.0 [M+H]+.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. custompartitioned between water/methylene chloride
  3. washThe organics were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification by flash chromatography (1-5% methanol/methylene chloride)

出典と根拠

ORDレコード
ord-ffdaa4444e3548e5a0996494f2ff854a
出典データセット
uspto-grants-2013_06
特許番号
US08461162B2

反応ノート

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