Sodium hydride → HCID 59497554, 화합물

HRID 1747350노트

반응식

HRID 1747350 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 59497554HCID 59497554, 화합물수율 6.2%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

반응 조건

온도
120 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-8f8c4c789dde41e780d856b907f9a1e2
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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