Sodium Carbonate → N,N-Dimethyl-6-((E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)naphthalen-2-amine

HRID 641813Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([N:12]([CH3:14])[CH3:13])[CH:6]=[CH:5]2.[CH3:15][C:16]1[N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]([CH3:23])=[CH:19][C:20]=1[CH:21]=[CH2:22].C([O-])([O-])=O.[Na+].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2].CN(C=O)C>[CH3:13][N:12]([CH3:14])[C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2](/[CH:22]=[CH:21]/[C:20]3[CH:19]=[C:18]([CH3:23])[N:17]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:16]=3[CH3:15])[CH:3]=2)[CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Dry DMF (10 mL) was added by syringe to the mixture of 6-bromo-N,N-dimethylnaphthalen-2-amine (200 mg, 0.8 mmol), 2,5-dimethyl-1-phenyl-3-vinyl-1H-pyrrole (236 mg, 1.2 mmol), Na2CO3 (254 mg, 2.4 mmol), n-Bu4NCl (224 mg, 0.8 mmol) and Pd(OAc)2 (8 mg, 0.33 mmol). The reaction mixture was stirred at 100° C. for 3 hrs, then quenched with water (20 mL) and extracted with EtOAc. The organic layer was washed with brine and dried over anhydrous Na2SO4. After purified by column chromatography (hexane/EtOAc=500:1), the target compound was obtained as brown yellow solid (50 mg, 17%). MS [M+]=366, LC-MS: tR=3.28 min.

Workup

customquenched with water (20 mL)
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over anhydrous Na2SO4
customAfter purified by column chromatography (hexane/EtOAc=500:1)

Sources & evidence

ORD record: ord-26113b85d03d45cb9a16f6db045972a0
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696227B2

Reaction notes

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