Sodium hydride → 1-(3-bromo-6-methoxy-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol

HRID 1752216Notes

Reaction equation

HRID 1752216 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3.[O:19]1[CH2:21][CH:20]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([CH2:21][CH:20]([OH:19])[CH2:22][NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([O:17][CH3:18])=[CH:11][CH:10]=3

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15886922HCID 15886922, compoundHCID 18522547N-(oxiran-2-ylmethyl)aniline

Product 1

HCID 712542941-(3-bromo-6-methoxy-9H-carbazol-9-yl)-3-(phenylamino)propan-2-olYield 31.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (0.0023 g of 60% suspension (in oil), 0.093 mmol) was added to a solution of 3-bromo-6-methoxy-9H-carbazole (0.014 g, 0.052 mmol) in anhydrous THF (0.1 mL) at 0° C. and stirred for 30 min. A solution of N-(oxiran-2-ylmethyl)aniline (0.0093 g, 0.062 mmol) in anhydrous THF (0.1 mL) was added dropwise to the reaction mixture. The reaction was warmed to room temperature and stirred for 48 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organics were concentrated and purified by chromatography (SiO2, 0-30% EtOAc/Hexane) to afford the title compound (0.007 g, 25%).

Workup

  1. stirringstirred for 48 h
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. concentrationThe combined organics were concentrated
  5. custompurified by chromatography (SiO2, 0-30% EtOAc/Hexane)

Sources & evidence

ORD record
ord-c8c011da2ce740adba6f549f70e0ce75
Source dataset
uspto-grants-2015_10
Patent number
US09162980B2

Reaction notes

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