Lithium hydroxide, monohydrate → 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(pyridin-4-ylamino)propan-2-ol

HRID 404296Notes

Reaction equation

HRID 404296 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][N:29]=[CH:28][CH: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.CCOC(C)=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][N:29]=[CH:28][CH: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

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 58065857HCID 58065857, compound

Product 1

HCID 468517181-(3,6-dibromo-9H-carbazol-9-yl)-3-(pyridin-4-ylamino)propan-2-ol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound of Example 41 was prepared as follows. LiOH.H2O (0.0157 g, 0.373 mmol) was added to 5-((3,6-dibromo-9H-carbazol-9-yl)methyl)-3-(pyridin-4-yl)oxazolidin-2-one (0.0187 g, 0.0373 mmol) in a mixture of 428 μL THF and 48 μL H2O (v/v=9:1). The mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with 30 mL EtOAc and washed with brine 3×30 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which did not require purification (0.0013 g white solid, 7.3%).

Workup

  1. washwashed with brine 3×30 mL
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-4e338ced2f934c13a5b92ca0a02e5295
Source dataset
uspto-grants-2014_06
Patent number
US08748473B2

Reaction notes

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