Tetrahydrofuran → 2-(aminomethyl)-5-bromo-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

HRID 1811137노트

반응식

HRID 1811137 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([CH:18]=O)[CH2:8][C:9]=1[NH:10]2.C([O-])(=O)C.[NH4+:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C1COCC1>C(Cl)Cl>[NH2:24][CH2:18][CH:7]1[CH2:6][CH2:5][C:4]2[C:3]3[C:11](=[C:12]([C:15]([NH2:17])=[O:16])[CH:13]=[CH:14][C:2]=3[Br:1])[NH:10][C:9]=2[CH2:8]1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 517165Ammonium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 866429585-bromo-2-formyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

생성물 1

HCID 666059472-(aminomethyl)-5-bromo-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide수율 13%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Step 3 A solution of crude 5-bromo-2-formyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (1 g, 3.11 mmol) in DCM (20 mL) was treated with ammonium acetate (3.60 g, 46.7 mmol) and sodium triacetoxyborohydride (0.990 g, 4.67 mmol) at rt and stirred for 10 min. THF (2 mL) was added to try to dissolve the starting material, but no reaction was observed after 1 h. The mixture was concentrated and the residue was dissolved in DMSO (10 mL). Additional sodium triacetoxyborohydride (500 mg) was added and the mixture was stirred at rt overnight. The mixture was diluted with water and the precipitate was removed by filtration. The filtrate was treated with 1 M aqueous sodium hydroxide and extracted three times with EtOAc. The combined organic phases were washed with water, dried and concentrated to provide 2-(aminomethyl)-5-bromo-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a white solid (130 mg, 13%), used without further purification. Mass spectrum m/z 322, 324 (M+H)+.

후처리

  1. dissolutionto dissolve the starting material
  2. waitno reaction was observed after 1 h
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in DMSO (10 mL)
  5. additionAdditional sodium triacetoxyborohydride (500 mg) was added
  6. stirringthe mixture was stirred at rt overnight
  7. additionThe mixture was diluted with water
  8. customthe precipitate was removed by filtration
  9. additionThe filtrate was treated with 1 M aqueous sodium hydroxide
  10. extractionextracted three times with EtOAc
  11. washThe combined organic phases were washed with water
  12. customdried
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c2a4e14b25f640018112feab68accac5
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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