N-bromobutanimide → tert-butyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505817

반응식

HRID 505817 반응식
[CH:1]1([C:7]2[C:8]3[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][C:9]=3[NH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(NC(=NC(C)C)O[C:24]([CH3:27])([CH3:26])[CH3:25])(C)C.C1C(=O)N([Br:39])C(=O)C1>C1COCC1.C(Cl)Cl>[Br:39][C:11]1[NH:10][C:9]2[CH:12]=[C:13]([C:15]([O:17][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:16])[S:14][C:8]=2[C:7]=1[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

6

반응물 3

HCID 67184N-bromobutanimideHCID 110417822-tert-Butyl-1,3-diisopropylisoureaHCID 586790966-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

생성물 1

HCID 68470696tert-butyl 5-bromo-6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylate수율 37%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution (0.2 M) of 6-cyclohexyl-4H-thieno[3,2-b]pyrrole-2-carboxylic acid (prepared as described in example 14, step 8) in THF was treated with tert-butyl N,N′-diisopropylimidocarbamate (2 eq.). The reaction mixture was heated to reflux for 1 h. After cooling down, the mixture was filtered trough a pad of silica gel and washed with AcOEt. Evaporation under reduced pressure of the filtrate gave a residue that was dissolved in DCM. The resulting solution (0.2 M) was cooled at 0° C. and treated with NBS (1 eq.). The reaction mixture was stirred at 0° C. for 1 h, then it was quenched with aqueous Na2S2O3 (saturated solution) and extracted with AcOEt. The combined organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine and dried. Evaporation of the solvent under reduced pressure afforded the title compound (37%) as a solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. temperatureAfter cooling down
  4. filtrationthe mixture was filtered trough a pad of silica gel
  5. washwashed with AcOEt
  6. customEvaporation under reduced pressure of the filtrate
  7. customgave a residue that
  8. customit was quenched with aqueous Na2S2O3 (saturated solution)
  9. extractionextracted with AcOEt
  10. washThe combined organic phase was washed with aqueous Na2S2O3 (saturated solution) and brine
  11. customdried
  12. customEvaporation of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-1df4ca85c96f422b947e708aae27cc8a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781431B2

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