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

HRID 661978

反応式

HRID 661978 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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(3H)-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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-5a000805a5ee4f41902c368f0ec51fda
出典データセット
uspto-grants-2011_12
特許番号
US08084620B2

関連ノート

読み込み中…