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

HRID 1811137ノート

反応式

HRID 1811137 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c2a4e14b25f640018112feab68accac5
出典データセット
uspto-grants-2013_01
特許番号
US08362065B2

反応ノート

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