Sodium Carbonate → HCID 67034134、化合物

HRID 539100ノート

反応式

HRID 539100 の反応式
Br[C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:11]3[C@@H:15]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=4)[CH2:14][O:13][C:12]3=[O:23])=[N:7][C:6]=12.[F:24][C:25]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[CH:27][C:26]=1[C:40]1[N:44]=[CH:43][N:42]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[N:41]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[F:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:3]=[N:4][N:5]3[CH:10]=[CH:9][C:8]([N:11]4[C@@H:15]([C:16]5[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=5)[CH2:14][O:13][C:12]4=[O:23])=[N:7][C:6]=23)[CH:28]=[CH:27][C:26]=1[C:40]1[N:44]=[CH:43][N:42]([CH2:45][O:46][CH2:47][CH2:48][Si:49]([CH3:52])([CH3:51])[CH3:50])[N:41]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 67034012HCID 67034012、化合物HCID 67034163(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one

生成物 1

HCID 67034134HCID 67034134、化合物収率 55%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To a solution of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (6.7 g, 18 mmol) and 3-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole (11 g, 27 mmol) in dioxane (150 mL) was added sodium carbonate (44 ml, 89 mmol) (2 M in water) and the reaction mixture bubbled with nitrogen gas for 30 minutes, followed by addition of 750 mg each of Pd2 dba3 and X-phos, and the reaction heated to 80° C. while the nitrogen purge continued. The reaction was poured into water (150 mL) and extracted with ethyl acetate (400 mL). The organic layer was washed with water (100 mL), brine (100 mL), dried over MgSO4 and concentrated in vacuo. The material was chromatographed using a gradient of 70% EtOAc/DCM to EtOAc as eluent to yield (S)-3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(5-fluoropyridin-2-yl)oxazolidin-2-one (5.8 g, 9.8 mmol, 55% yield).

後処理

  1. customthe reaction mixture bubbled with nitrogen gas for 30 minutes
  2. additionfollowed by addition of 750 mg each of Pd2 dba3 and X-phos
  3. custompurge
  4. additionThe reaction was poured into water (150 mL)
  5. extractionextracted with ethyl acetate (400 mL)
  6. washThe organic layer was washed with water (100 mL), brine (100 mL)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe material was chromatographed

出典と根拠

ORDレコード
ord-4a89b9010f684c54ba0be1b9bc854a34
出典データセット
uspto-grants-2014_10
特許番号
US08865726B2

反応ノート

読み込み中…