1,4-Dioxane → Methyl 4-(6-pyridin-3-ylpyrazolo[1,5-c]pyrimidin-3-yl)thiophene-2-carboxylate

HRID 1255859ノート

反応式

HRID 1255859 の反応式
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[S:12][CH:13]=2)O1.Br[C:20]1[CH:21]=[N:22][N:23]2[CH:28]=[C:27](C3C=NC=CC=3)[CH:26]=[N:25][C:24]=12.C(=O)(O)[O-].[Na+].O1[CH2:45][CH2:44]OCC1>>[N:22]1[CH:45]=[CH:44][CH:24]=[C:20]([N:25]2[CH:26]=[CH:27][C:28]3=[C:20]([C:9]4[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[S:12][CH:13]=4)[CH:21]=[N:22][N:23]3[CH2:24]2)[CH:21]=1

参加物

5

反応物 4

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 52911233Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylateHCID 687770603-Bromo-6-pyridin-3-ylpyrazolo[1,5-a]pyrimidine

生成物 1

HCID 68775345Methyl 4-(6-pyridin-3-ylpyrazolo[1,5-c]pyrimidin-3-yl)thiophene-2-carboxylate

反応条件

温度
85 °C

実験手順

A solution of methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate (1.09 g, 4.1 mmol) and 3-bromo-6-pyridin-3-ylpyrazolo[1,5-a]pyrimidine (1.1 g, 4.1 mmol) in dioxane (20 mL) and 1M aqueous sodium bicarbonate (12.2 mL, 12.2 mmol) was degassed with nitrogen and treated with palladium tetrakistriphenylphosphine (0.24 g, 0.20 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 methyl 4-(6-pyridin-3-ylpyrazolo[1,5-c]pyrimidin-3-yl)thiophene-2-carboxylate. LC-MS SIMS: m/z 337.1 [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-05c14e3c721f47ba83f5e5b536ae1fe4
出典データセット
uspto-grants-2013_06
特許番号
US08461162B2

反応ノート

読み込み中…