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

HRID 1255858노트

반응식

HRID 1255858 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-ffdaa4444e3548e5a0996494f2ff854a
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461162B2

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