1,2-Dibromoethane → HCID 66604575, compound

HRID 2410885Notes

Reaction equation

HRID 2410885 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:30]([NH2:32])=[O:31])[C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][CH:17]=[C:16]([N:22]2[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]2)[CH:15]=4)[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[Br:39][CH2:40][CH2:41]Br.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Br:39][CH2:40][CH2:41][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:10]=[C:11]([C:30]([NH2:32])=[O:31])[C:12]3[NH:13][C:14]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][CH:17]=[C:16]([N:22]2[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]2)[CH:15]=4)=[CH:3][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 66604985HCID 66604985, compound

Product 1

HCID 66604575HCID 66604575, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 ml round bottom flask was loaded with 3-(3-chloro-4-hydroxyphenyl)-7-(1,1-dioxo-thiomorpholino)-9H-carbazole-1-carboxamide (49.4 mg, 0.084 mmol, Example 408B), K2CO3 (150 mg, 1.085 mmol), DMF (6 ml) and 1,2-dibromoethane (0.09 ml, 1.044 mmol) and stirred at room temperature for 4.5 hours. The reaction mixture was poured into a separating funnel that was loaded with 100 ml water+citric acid (0.5 M solution in water) (10 ml, 5.00 mmol) and extracted with ethyl acetate. The organic layer was washed with dilute (1+5) aq. NaHCO3 solution, then brine, dried over MgSO4, filtered and evaporated to dryness to give 48.6 mg 3-(4-(2-bromoethoxy)-3-chlorophenyl)-7-(1,1-dioxo-thiomorpholino)-9H-carbazole-1-carboxamide, which was used without further purification. Estimated purity (from LCMS) ˜90%. MS (ESI) m/e+=576/578/580, m/e−=574/576/578 consistent with isotope pattern for 1 Br and 1 Cl.

Workup

  1. additionThe reaction mixture was poured into a separating funnel that
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed
  4. additionwith dilute (1+5) aq. NaHCO3 solution
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0cfb63d65d324777be4cffcd6f753efa
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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