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

HRID 62201Notes

Reaction equation

HRID 62201 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:27]=[N:28][CH:29]=[CH:30][CH:31]=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:27]=[N:28][CH:29]=[CH:30][CH:31]=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 2

HCID 168937Lithium hydroxide, monohydrateHCID 58065880HCID 58065880, compound

Product 1

HCID 468517171-(3,6-dibromo-9H-carbazol-9-yl)-3-(pyridin-3-ylamino)propan-2-olYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound of Example 40 was prepared as follows. LiOH.H2O (0.0097 g, 0.231 mmol) was added to 5-((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-3-yl)oxazolidin-2-one (0.0116 g, 0.0231 mmol) in a mixture of 265 μL THF and 29 μL H2O (v/v=9:1). The mixture was stirred at room temperature for 7 days. The reaction mixture purified by silica gel chromatography using CHCl3/MeOH as elute to afford 0.0087 g white solid as product, yield 79.3%.

Workup

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

Sources & evidence

ORD record
ord-68608b1e5d63467192413535527e1716
Source dataset
uspto-grants-2016_09
Patent number
US09446042B2

Reaction notes

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