Water → 4-bromo-7-(4-hydroxy-2,2-dimethylbutanamido)-9H-carbazole-1-carboxamide

HRID 1811158

반응식

HRID 1811158 반응식
Br.[NH2:2][C:3]1[CH:15]=[C:14]2[C:6]([C:7]3[C:8]([Br:19])=[CH:9][CH:10]=[C:11]([C:16]([NH2:18])=[O:17])[C:12]=3[NH:13]2)=[CH:5][CH:4]=1.[CH3:20][C:21]1([CH3:27])[CH2:25][CH2:24][O:23][C:22]1=[O:26].C[Al](C)C.O>C1COCC1>[Br:19][C:8]1[C:7]2[C:6]3[C:14](=[CH:15][C:3]([NH:2][C:22](=[O:26])[C:21]([CH3:27])([CH3:20])[CH2:25][CH2:24][OH:23])=[CH:4][CH:5]=3)[NH:13][C:12]=2[C:11]([C:16]([NH2:18])=[O:17])=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 947462,2-Dimethyl-4-butyrolactoneHCID 16682925TrimethylaluminumHCID 666057197-amino-4-bromo-9H-carbazole-1-carboxamide hydrobromide

생성물 1

HCID 593750144-bromo-7-(4-hydroxy-2,2-dimethylbutanamido)-9H-carbazole-1-carboxamide수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

A mixture of 7-amino-4-bromo-9H-carbazole-1-carboxamide hydrobromide (Example 54-2, 500 mg, 1.299 mmol) and 3,3-dimethyldihydrofuran-2(3 H)-one (222 mg, 1.948 mmol) in THF (10 mL) was treated with trimethylaluminum (2 M in toluene, 562 mg, 7.79 mmol) dropwise at rt. The mixture was heated at 50° C. for 1.5 h, cooled to rt and treated with water. The mixture was filtered through Celite and the solids were washed thoroughly with DCM and methanol. The filtrate was washed with water, dried and concentrated, and the residue was purified by column chromatography (eluting with a gradient from DCM to 10% ammonia-methanol-DCM) to provide 4-bromo-7-(4-hydroxy-2,2-dimethylbutanamido)-9H-carbazole-1-carboxamide as a yellow solid (250 mg, 46%). Mass spectrum m/z 418, 420 (M+H)+.

후처리

  1. temperaturecooled to rt
  2. filtrationThe mixture was filtered through Celite
  3. washthe solids were washed thoroughly with DCM and methanol
  4. washThe filtrate was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography (
  8. washeluting with a gradient from DCM to 10% ammonia-methanol-DCM)

출처 및 근거

ORD 기록
ord-7119e3e13a6f48429d00bec535f949c1
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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