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Styrylboronic acid → (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide

HRID 1778300
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인쇄 미리보기

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HRID 1778300 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([N:14]([O:16][CH3:17])[CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH:18](/B(O)O)=[CH:19]\[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1COCC1.C(Cl)Cl.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:17][O:16][N:14]([CH3:15])[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:13]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 5702628Styrylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 22031701Potassium phosphate, tribasic, monohydrateHCID 1183240674-bromo-N-methoxy-N-methylquinoline-6-carboxamide

생성물 1

HCID 118323977(E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide

시약·촉매·용매 4

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매

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온도
35 °C

실험 절차

A mixture of 4-bromo-N-methoxy-N-methylquinoline-6-carboxamide (155 mg, 0.525 mmol), (E)-styrylboronic acid (155 mg, 1.05 mmol), Pd(OAc)2 (11.8 mg, 0.053 mmol), SPhos (43 mg, 0.105 mmol) and K3PO4.H2O (334 mg, 1.58 mmol) in anhydrous THF (5 mL) was heated at 35° C. overnight. The reaction was diluted with DCM and water. The organics were washed with water and concentrated. The resulting residue was purified by silica column chromatography (40-55% EtOAc/hexanes) to yield (E)-N-methoxy-N-methyl-4-styrylquinoline-6-carboxamide. (ES, m/z) 319.0 [M+H]+

후처리

  1. washThe organics were washed with water
  2. concentrationconcentrated
  3. customThe resulting residue was purified by silica column chromatography (40-55% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-2f2c80a0ab7249359877fa350a75d7bb
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266835B2

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