Sodium Carbonate → 4-(1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 68747

반응식

HRID 68747 반응식
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[C:11]([O:15][C:16]([N:18]1[CH2:19][CH:20]=[C:21]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[N:7][NH:8]3)=[CH:4][CH:3]=2)[CH2:22][CH2:23]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 178424716-Bromo-1H-indazole

생성물 1

HCID 674494164-(1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

To a mixture of 6-bromoindazole (2.0 g, 10.2 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.5 g, 11.2 mmol) and Pd(PPh3)4 (1.2 g, 1.0 mmol) under N2 were added 1,4-dioxane (80 mL), followed by addition of K2CO3 (2 M in H2O, 20 mL, 40 mmol). The resulting mixture was heated at 110° C. for 16 h, then cooled to room temperature. The resulting mixture was then treated with saturated Na2CO3 aqueous solution. The resulting mixture was extracted with EtOAc (3×). The combined extracts were washed with brine and then dried over Na2SO4. The resulting mixture was filtered, concentrated under reduced pressure, and the residue purified by flash chromatography on silica-gel (gradient eluent heptane to 60% EtOAc in heptane) to yield 4-(1H-indazol-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as brownish foam solid.

후처리

  1. temperaturecooled to room temperature
  2. extractionThe resulting mixture was extracted with EtOAc (3×)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe resulting mixture was filtered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue purified by flash chromatography on silica-gel (gradient eluent heptane to 60% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-4a50c4d2f95c495ca72eca4eeaccd606
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822447B2

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