1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Trifluoromethyl)benzo[b]thiophene

HRID 1908231노트

반응식

HRID 1908231 반응식
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:14]=[CH:13][C:6]2[S:7][C:8](C(O)=O)=[CH:9][C:5]=2[CH:4]=1.N12CCCN=C1CCCCC2>CC(N(C)C)=O.Cl>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:14]=[CH:13][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1

참가 물질

5

반응물 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27830435-(Trifluoromethyl)-1-benzothiophene-2-carboxylic acid

생성물 1

HCID 117456995-(Trifluoromethyl)benzo[b]thiophene수율 74.3%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 31374Dimethylacetamide용매

반응 조건

온도
200 °C

실험 절차

A mixture of 5-trifluoromethyl-benzo[b]thiophene-2-carboxylic acid (2.00 g, 8.12 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (5.0 mL, 34 mmol) in DMA (13 mL) was heated via microwave irradiation at 200° C. for 1 h. The reaction was cooled to rt, diluted with HCl (1 N aq., 20 mL) and extracted with EtOAc (20 mL). The organic layer was washed with water (10 mL), dried (Na2SO4) and concentrated. The residue was taken up in Et2O (25 mL) and washed with water (25 mL). The aqueous layer was extracted with Et2O (10 mL×2). The combined Et2O layers were dried (Na2SO4) and concentrated. The crude material was purified (FCC) to yield the title compound (1.22 g, 74%).

후처리

  1. temperatureThe reaction was cooled to rt
  2. extractionextracted with EtOAc (20 mL)
  3. washThe organic layer was washed with water (10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. washwashed with water (25 mL)
  7. extractionThe aqueous layer was extracted with Et2O (10 mL×2)
  8. dry with materialThe combined Et2O layers were dried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude material was purified (FCC)

출처 및 근거

ORD 기록
ord-0c323f83306e40089a78efb900a26d77
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598202B2

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