Cesium carbonate → tert-Butyl 2-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 1918909노트

반응식

HRID 1918909 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][C:4]=2[N:3]=1.Br[C:20]1[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=[C:24]([Br:26])[CH:25]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)Cl.O1CCOCC1>[Br:26][C:24]1[CH:25]=[C:20]([NH:1][C:2]2[CH:11]=[CH:10][C:9]3[CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][C:4]=3[N:3]=2)[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 58043778tert-Butyl 2-Amino-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

생성물 1

HCID 58044254tert-Butyl 2-(5-Bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

To a round-bottomed flask equipped with a stirring bar, 158b (851 mg, 3.41 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (1.37 g, 5.12 mmol), Pd2(dba)3 (312.5 mg, 0.341 mmol), XantPhos (316 mg, 0.546 mmol), Cs2CO3 (3.67 g, 11.3 mmol) and dioxane (17 mL) were added. The reaction mixture was heated at 100° C. overnight. DCM (200 mL) was added to the resulting mixture was washed with water (30 mL×3). DCM (200 mL) was added and the resulting mixture was washed with water (30 mL×3), brine (30 mL×1), dried over MgSO4, filtered, and removed solvent in vacuo. DCM/ether (1:2, 5 mL) was added followed by sonication, the precipitation was filtered as 158c, green solids, 865 mg (58%).

후처리

  1. customTo a round-bottomed flask equipped with a stirring bar
  2. washwas washed with water (30 mL×3)
  3. additionDCM (200 mL) was added
  4. washthe resulting mixture was washed with water (30 mL×3), brine (30 mL×1)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customremoved solvent in vacuo
  8. additionDCM/ether (1:2, 5 mL) was added
  9. customfollowed by sonication
  10. customthe precipitation
  11. filtrationwas filtered as 158c, green solids, 865 mg (58%)

출처 및 근거

ORD 기록
ord-8908064acb4e44eb892f2b273633410c
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618107B2

반응 노트

불러오는 중…