Cesium carbonate → HCID 72203564、化合物

HRID 629097ノート

反応式

HRID 629097 の反応式
Br[C:2]1[C:3]([C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:26]1[CH:31]=[C:30](B(O)O)[CH:29]=[N:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O.O1CCOCC1>[N:26]1[CH:31]=[C:30]([C:2]2[C:3]([C:22]([F:25])([F:24])[F:23])=[N:4][CH:5]=[C:6]([CH:21]=2)[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])[CH:29]=[N:28][CH:27]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 89907016HCID 89907016、化合物

生成物 1

HCID 72203564HCID 72203564、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
70 °C

実験手順

5-Bromo-N-(4-(trifluoromethoxy)phenyl)-6-(trifluoromethyl)nicotinamide (Stage 57.1, 125.7 mg, 0.293 mmol), pyrimidin-5-ylboronic acid (43.6 mg, 0.352 mmol), Cs2CO3 (191 mg, 0.586 mmol), PdCl2(dppf)-(CH2Cl2) (23.92 mg, 0.029 mmol), water (2 mL) and dioxane (8 mL) were added to a vial, which was sealed, evacuated/purged with argon and the RM was stirred at 70° C. for 2.5 h. The solvent was evaporated off under reduced pressure to give a residue which was treated with water and extracted with EtOAc. The combined extracts were washed with water and brine, dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 25 g, n-hexane/EtOAc) and recrystallized from n-hexane/EtOAc to give the title compound as a pink powder. UPLC-MS (Condition 2) tR=1.07 min, m/z=429 [M+H]+.

後処理

  1. customwas sealed
  2. customevacuated/purged with argon
  3. customThe solvent was evaporated off under reduced pressure
  4. customto give a residue which
  5. extractionextracted with EtOAc
  6. washThe combined extracts were washed with water and brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was evaporated off under reduced pressure
  9. customto give the crude product which
  10. customwas purified by flash chromatography (Silica gel column, 25 g, n-hexane/EtOAc)
  11. customrecrystallized from n-hexane/EtOAc

出典と根拠

ORDレコード
ord-32c65b7f729545b59967f6def667683c
出典データセット
uspto-grants-2016_04
特許番号
US09315489B2

反応ノート

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