Bromomethyl 4-methoxyphenyl ketone → HCID 71254608, compound

HRID 2200527Notes

Reaction equation

HRID 2200527 reaction equation
[S:1]1[C:5]2[NH:6][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:8][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:18]>CN(C=O)C>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17](=[O:18])[CH2:16][N:6]2[C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:8][C:4]3[CH:3]=[CH:2][S:1][C:5]2=3)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 24758Sodium hydrideHCID 7164601methyl 6H-thieno[2,3-b]pyrrole-5-carboxylate

Product 1

HCID 71254608HCID 71254608, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 6H-thieno[2,3-b]pyrrole-5-carboxylate (100 mg, 0.55 mmol) in DMF (2 mL) was added sodium hydride (15 mg, 0.63 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour before 2-bromo-1-(4-methoxyphenyl)ethanone (251 mg, 1.1 mmol) was added. After 5 minutes, the reaction was allowed to warm to room temperature and stirred for 1 hour. The mixture was then poured into ice water and the resulting precipitate collected by filtration and washed with hexanes to yield methyl 6-[2-(4-methoxyphenyl)-2-oxoethyl]-6H-thieno[2,3-b]pyrrole-5-carboxylate (100 mg, 55% yield) as a white solid. ESI-MI m/z [M+H]+ 330.15. 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=8.8 Hz, 2H), 7.25 (s, 1H), 7.02 (d, J=5.3 Hz, 1H), 6.99 (d, J=8.8 Hz, 2H), 6.91 (d, J=5.3 Hz, 1H), 5.84 (s, 2H), 3.90 (s, 3H), 3.78 (s, 3H).

Workup

  1. additionwas added
  2. filtrationthe resulting precipitate collected by filtration
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-56de499641b146ed965e15114e8773f8
Source dataset
uspto-grants-2016_06
Patent number
US09359377B2

Reaction notes

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