Sodium hydride → HCID 59497554, compound

HRID 1747350Notes

Reaction equation

HRID 1747350 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15].[H-].[Na+].Br[CH2:20][C:21]1[C:26]2[S:27][CH:28]=[CH:29][C:25]=2[CH:24]=[CH:23][CH:22]=1>CC(N(C)C)=O.C(OCC)(=O)C>[S:27]1[C:26]2[C:21]([CH2:20][N:8]3[C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:16])[C:7]3=[O:15])=[CH:22][CH:23]=[CH:24][C:25]=2[CH:29]=[CH:28]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 107517617-(Bromomethyl)-1-benzothiopheneHCID 59497358HCID 59497358, compound

Product 1

HCID 59497554HCID 59497554, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (200 mg, 0.91 mmol) in DMA (5 ml) was added sodium hydride (60% oil dispersion, 55 mg, 1.4 mmol). The resulting mixture was stirred for 10 minutes at ambient temperature after which time 7-bromomethyl-benzo[b]thiophene (206 mg, 0.91 mmol) was added. The reaction was heated at 120° C. in a microwave for 20 minutes. Upon cooling to ambient temperature the reaction was diluted with ethyl acetate and washed with NaHCO3 (sat.) and brine. The aqueous phase was acidified using 1M HCl and extracted once with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 5% methanol/dichloromethane). The product-containing fractions were combined and concentrated to give 20 mg (6%) of the desired product. LCMS (ESMS): m/z 353.41 (M+H+).

Workup

  1. additionwas added
  2. temperatureUpon cooling to ambient temperature the reaction
  3. washwashed with NaHCO3 (sat.) and brine
  4. extractionextracted once with ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified via column chromatography (silica gel, 5% methanol/dichloromethane)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8f8c4c789dde41e780d856b907f9a1e2
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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