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Ethyl Acetate → 4-Quinoxalin-6-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1038145
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HRID 1038145 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[N:5]2.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].C(OC(=O)C)C>O1CCOCC1.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH:21]=[C:22]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[N:5]3)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 6109396-BromoquinoxalineHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

생성물 1

HCID 576862004-Quinoxalin-6-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 2

HCID 11979704
Tetrakis(triphenylphosphine)palladium
촉매
HCID 69104347Dioxane ethanol water용매

반응 조건

온도
160 °C

실험 절차

A solution containing 6-bromo-quinoxaline (417 mg, 2.0 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (600 mg, 1.94 mmol), tetrakis [triphenylphosphine] palladium (108 mg, 0.1 mmol) and sodium carbonate (2 M solution, 3 mL) in 5 mL of dioxane/ethanol/water (7:3:1) was heated at 160° C. using microwave reactor for 15 minutes. After the reaction, ethylacetate was added and the mixture was filtered, washed with water. After concentration under vacuum, the product was purified using column chromatography (5% methanol in dichloromethane)

후처리

  1. customfor 15 minutes
  2. additionwas added
  3. filtrationthe mixture was filtered
  4. washwashed with water
  5. concentrationAfter concentration under vacuum
  6. customthe product was purified

출처 및 근거

ORD 기록
ord-deeeb938f15845adb91322ee86c4da9c
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546404B2

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