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 1020955ノート

反応式

HRID 1020955 の反応式
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]

参加物

7

反応物 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

生成物 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 ester収率 86.7%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-d07ee0f111ea4bc68c79d98e4a57c1f4
出典データセット
uspto-grants-2014_05
特許番号
US08716483B2

反応ノート

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