Ammonia → 1-amino-3-(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol

HRID 62159Notes

Reaction equation

HRID 62159 reaction equation
[NH3:1].[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH2:17][CH:18]3[CH2:20][O:19]3)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][C:11]([Br:16])=[CH:10][CH:9]=3>>[NH2:1][CH2:20][CH:18]([OH:19])[CH2:17][N:7]1[C:6]2[CH:5]=[CH:4][C:3]([Br:2])=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[C:11]([Br:16])[CH:12]=2

Participants

3

Reactant 2

HCID 222AmmoniaHCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

Product 1

HCID 468526711-amino-3-(3,6-dibromo-9H-carbazol-9-yl)propan-2-olYield 65.4%

Conditions

Temperature
100 °C

Procedure

A solution of NH3 (9.4 mL of 7M in MeOH, 65.6 mmol) was added to 3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole (0.500 g, 1.31 mmol). The vial was tightly sealed and the reaction mixture was heated to 100° C. and stirred for 1 hour. Volatile components were removed under vacuum. The residue was suspended in CH2Cl2 and the white precipitate was filtered. The filtrate was saved and CH2Cl2 was removed under vacuum to afford 0.3413 g white solid as crude product, which contained about 50% unidentified side-product. This crude product was used as is in next step without any further purification. Purification by flash chromatography on silica gel provided pure material.

Workup

  1. customThe vial was tightly sealed
  2. customVolatile components were removed under vacuum
  3. filtrationthe white precipitate was filtered
  4. customCH2Cl2 was removed under vacuum

Sources & evidence

ORD record
ord-2306a2b63a2a484b88f8aec9b5dfd159
Source dataset
uspto-grants-2016_09
Patent number
US09446022B2

Reaction notes

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