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

HRID 1778300
Notes
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Reaction equation

HRID 1778300 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

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]+

Workup

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

Sources & evidence

ORD record
ord-2f2c80a0ab7249359877fa350a75d7bb
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266835B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes