Cesium carbonate → Ethyl 6'-{[(ethylamino)carbonyl]amino}-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxylate

HRID 2243036노트

반응식

HRID 2243036 반응식
Br[C:2]1[C:3]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)=[CH:4][C:5]([NH:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][CH:36]=[C:37]([CH:43]=2)[C:38]([O:40][CH2:41][CH3:42])=[O:39])O1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:12]([NH:11][C:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([C:33]2[CH:34]=[N:35][CH:36]=[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:43]=2)=[C:3]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)[CH:4]=1)=[O:10])[CH3:13]

참가 물질

4

반응물 3

HCID 10796Cesium carbonateHCID 3816953Ethyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylateHCID 592085041-(5-Bromo-4-(4-phenylthiazol-2-yl)pyridin-2-yl)-3-ethylurea2회

생성물 1

HCID 59208481Ethyl 6'-{[(ethylamino)carbonyl]amino}-4'-(4-phenyl-1,3-thiazol-2-yl)-3,3'-bipyridine-5-carboxylate수율 100.6%

반응 조건

온도
100 °C

실험 절차

N-[5-bromo-4-(4-phenyl-1,3-thiazol-2-yl)pyridin-2-yl]-N′-ethylurea (Intermediate 69, 0.17 g, 0.42 mmol), ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (0.14 g, 0.51 mmol), tetrakis triphenyl phosphine palladium (0.024 g, 0.02 mmol), and cesium carbonate (0.165 g, 0.51 mmol) were combined in a microwave vial and degassed with nitrogen. 1,4-dioxane:water (4:1, 2.5 mL) was added to the mixture and the reaction mixture was heated to 100° C. for 60 minutes. The reaction mixture was partitioned between water and ethyl acetate and the layers separated. The organic layer was washed with saturated NaHCO3, water, and brine, then dried over magnesium sulfate. The organic layer was concentrated to form a precipitate, and the resulting solids were filtered and then washed with acetonitrile followed by chloroform to yield 200 mg of the title compound as an off-white solid. LC/MS (ES+)[(M+H)+]: 474 for C25H23N5O3S. 1H NMR (300 MHz, CHCl3): 1.28 (t, 3H), 1.39 (t, 3H), 3.44-3.49 (m, 2H), 4.41 (q, 2H), 7.31-7.39 (m, 2H), 7.52 (s, 1H), 7.62 (d, 2H), 8.17 (s, 1H), 8.28 (t, 1H), 8.32 (t, 1H), 8.4 (s, 1H), 8.71 (d, 1H), 8.73 (d, 1H), 9.23 (d, 1H), 9.27 (s, 1H).

후처리

  1. customdegassed with nitrogen
  2. addition1,4-dioxane:water (4:1, 2.5 mL) was added to the mixture
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customthe layers separated
  5. washThe organic layer was washed with saturated NaHCO3, water, and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe organic layer was concentrated
  8. customto form a precipitate
  9. filtrationthe resulting solids were filtered
  10. washwashed with acetonitrile

출처 및 근거

ORD 기록
ord-ac4df2b0165d4e2aa519a8944164f906
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674801B2

반응 노트

불러오는 중…