Triethylamine → 5-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-one

HRID 332095Notes

Reaction equation

HRID 332095 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][CH2:14][CH:15]([OH:32])[CH2:16][N:17]1[C:29]2[CH:28]=[CH:27][C:26]([Br:30])=[CH:25][C:24]=2[C:23]2[C:18]1=[CH:19][CH:20]=[C:21]([Br:31])[CH:22]=2.CCN(CC)CC.C(Cl)Cl.CCOC(C)=O>C(Cl)Cl>[Br:31][C:21]1[CH:20]=[CH:19][C:18]2[N:17]([CH2:16][CH:15]3[O:32][C:2](=[O:4])[NH:13][CH2:14]3)[C:29]3[C:24]([C:23]=2[CH:22]=1)=[CH:25][C:26]([Br:30])=[CH:27][CH:28]=3

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 21226138Dichloromethane ethylacetateHCID 468526711-amino-3-(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol

Product 1

HCID 580971985-((3,6-dibromo-9H-carbazol-9-yl)methyl)oxazolidin-2-oneYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

A solution of triphosgene (0.0890 g, 0.300 mmol, 0.35 equiv) in 2 mL anhydrous CH2Cl2 was added dropwise to a solution of 1-amino-3-(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol (0.3413 g, 0.857 mmol) and Et3N (0.1909 g, 1.886 mmol) in 1 mL CH2Cl2 under N2 atmosphere at 4° C. The reaction mixture was stirred for 15 min at 4° C. and then warmed to room temperature and stirred for 1 hour. CH2Cl2 was removed under vacuum. Saturated NH4Cl (5 mL) and 10 mL EtOAc was added to the residue and stirred for 20 min. Then the aqueous layer was separated and the organic layer was washed with water 2×10 mL. The combined aqueous layers were extracted with EtOAc, dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using CH2Cl2/EtOAc to afford 0.1173 g white solid, yield 20.0% over 2 steps.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 1 hour
  3. customCH2Cl2 was removed under vacuum
  4. additionSaturated NH4Cl (5 mL) and 10 mL EtOAc was added to the residue
  5. stirringstirred for 20 min
  6. customThen the aqueous layer was separated
  7. washthe organic layer was washed with water 2×10 mL
  8. extractionThe combined aqueous layers were extracted with EtOAc
  9. dry with materialdried over anhydrous Na2SO4
  10. customevaporated
  11. customto afford the crude product, which

Sources & evidence

ORD record
ord-11b18c3494444d79b7a61a5b44b12f1a
Source dataset
uspto-grants-2014_11
Patent number
US08877797B2

Reaction notes

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