Dichloromethane → 4-[5-(1-methyl-1H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1020955노트

반응식

HRID 1020955 반응식
Br[C:2]1[S:6][C:5]([C:7]2[N:11]=[CH:10][N:9]([CH3:12])[N:8]=2)=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].ClCCl.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>O1CCOCC1>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH:22]=[C:23]([C:2]2[S:6][C:5]([C:7]3[N:11]=[CH:10][N:9]([CH3:12])[N:8]=3)=[CH:4][CH:3]=2)[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

참가 물질

7

반응물 5

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 583719633-(5-bromo-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole

생성물 1

HCID 583719164-[5-(1-methyl-1H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester수율 86.7%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

To a large pressure flask were charged compound 3-(5-bromo-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole (3.1 g, 12.8 mmols) (5BW), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.6 g, 11.65 mmols), [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium (II), complex with dichloromethane (1:1) (0.475 g, 0.89 mmols), Na2CO3 (8.5 ml) and dioxane (40 ml). The mixture was briefly degassed with Ar for ˜0.5 minute, capped and stirred at 80° C. overnight. After cooling, the reaction mixture was diluted with EtOAc and brine. Organic layer was isolated, and dried MgSO4. After concentration, the residue was purified on silica gel. Elution with EtOAc (100%) gave the desired product (6BW) (3.5 g).

후처리

  1. customThe mixture was briefly degassed with Ar for ˜0.5 minute
  2. customcapped
  3. temperatureAfter cooling
  4. additionthe reaction mixture was diluted with EtOAc and brine
  5. customOrganic layer was isolated
  6. concentrationAfter concentration
  7. customthe residue was purified on silica gel
  8. washElution with EtOAc (100%)

출처 및 근거

ORD 기록
ord-d07ee0f111ea4bc68c79d98e4a57c1f4
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716483B2

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