Water → 2'-Methoxy-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

HRID 629104ノート

反応式

HRID 629104 の反応式
Br[C:2]1[CH:3]=[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].[CH3:22][O:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1>[CH3:22][O:23][C:24]1[C:29]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)=[CH:28][CH:27]=[CH:26][N:25]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 46840185-bromo-N-(4-(trifluoromethoxy)phenyl)nicotinamide

生成物 1

HCID 722035682'-Methoxy-N-(4-(trifluoromethoxy)phenyl)-[3,3'-bipyridine]-5-carboxamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

5-Bromo-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 61.1, 90 mg, 0.25 mmol), 2-methoxypyridin-3-ylboronic acid (45.9 mg, 0.300 mmol), K2CO3 (69.1 mg, 0.500 mmol), PdCl2(dppf)-(CH2Cl2) (20.42 mg, 0.025 mmol), water (0.6 mL) and dioxane (3 mL) were added to a vial, which was sealed, evacuated/purged with argon and the RM was stirred at 60° C. for 1 h. The RM 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, 15 g, EtOAc) to afford the title compound as a white powder. UPLC-MS (Condition 2) tR=1.1 min, m/z=390.2 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 3.93 (s, 3H) 7.19 (dd, J=7.23, 4.89 Hz, 1H) 7.40 (d, J=8.99 Hz, 2H) 7.89 (m, J=9.00 Hz, 2H) 7.97 (dd, J=7.43, 1.96 Hz, 1H) 8.28 (dd, J=5.08, 1.96 Hz, 1H) 8.46 (t, J=2.15 Hz, 1H) 8.97 (d, J=1.95 Hz, 1H) 9.08 (d, J=2.35 Hz, 1H) 10.64 (s, 1H).

後処理

  1. customwas sealed
  2. customevacuated/purged with argon
  3. additionThe RM was treated with water
  4. extractionextracted with EtOAc
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was evaporated off under reduced pressure
  8. customto give the crude product which
  9. customwas purified by flash chromatography (Silica gel column, 15 g, EtOAc)

出典と根拠

ORDレコード
ord-5ce73bce7812443ba41dddd6cffd2e6f
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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