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

HRID 1778300
ノート
印刷プレビュー

反応式

HRID 1778300 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

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]+

後処理

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

出典と根拠

ORDレコード
ord-2f2c80a0ab7249359877fa350a75d7bb
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266835B2

反応ノート

読み込み中…

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