Potassium tert-butoxide → 4-(3-bromophenyl)-6,7-dimethoxy-3-(thiophen-2-yl)quinolin-2(1H)-one

HRID 1191331Notes

Reaction equation

HRID 1191331 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=2[NH:20][C:21](=[O:28])[CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=O)[CH:5]=[CH:6][CH:7]=1.CC([O-])(C)C.[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:10]3[C:11](=[CH:12][C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=3)[NH:20][C:21](=[O:28])[C:22]=2[C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66849274N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2-(thiophen-2-yl)acetamide

Product 1

HCID 668998014-(3-bromophenyl)-6,7-dimethoxy-3-(thiophen-2-yl)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{2-[(3-bromophenyl)carbonyl]-4,5-dimethoxyphenyl}-2-(thiophen-2-yl)acetamide (8 g, 17.4 mmol) in dry THF (80 mL) was added t-BuOK (6 g 52.1 mmol) in portions at 0° C. The reaction mixture was stirred for 1 hour and concentrated under reduced pressure. The residue was diluted with EtOAc (50 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuum to afford 4-(3-bromophenyl)-6,7-dimethoxy-3-(thiophen-2-yl)quinolin-2(1H)-one. MS (M+H)=442 and 444.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with EtOAc (50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-b1b5bf7b116f43a48ff1c5f680d4bf30
Source dataset
uspto-grants-2014_03
Patent number
US08680116B2

Reaction notes

Loading…