Tetrahydrofuran → 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(pyridin-2-ylamino)propan-2-ol

HRID 62162Notes

Reaction equation

HRID 62162 reaction equation
O[Li].O.[Br:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:19][CH:20]3[O:24]C(=O)[N:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[CH2:21]3)[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([Br:18])=[CH:12][CH:11]=3.C1COCC1>O>[Br:18][C:13]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:19][CH:20]([OH:24])[CH2:21][NH:22][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[C:8]3[C:16]([C:15]=2[CH:14]=1)=[CH:17][C:5]([Br:4])=[CH:6][CH:7]=3

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 580971855-((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-2-yl)oxazolidin-2-one

Product 1

HCID 468513841-(3,6-dibromo-9H-carbazol-9-yl)-3-(pyridin-2-ylamino)propan-2-olYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

LiOH.H2O (0.0076 g, 0.182 mmol, 10 equiv) was added to 5((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-2-yl)oxazolidin-2-one (0.0091 g, 0.0182 mmol) in a mixture of 2084, THF and 234, H2O (v/v=9:1). The mixture was stirred at room temperature for 7 days. The reaction mixture was purified by silica gel chromatography using CH2Cl2/EtOAc as elute to afford 0.0071 g white solid as product, yield 41.0%.

Workup

  1. customThe reaction mixture was purified by silica gel chromatography
  2. washas elute

Sources & evidence

ORD record
ord-7f7185a0ca44435c953bd9c851403978
Source dataset
uspto-grants-2016_09
Patent number
US09446022B2

Reaction notes

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