1,2-Dibromoethane → 3-(4-(2-bromoethoxy)-3-chlorophenyl)-7-morpholino-9H-carbazole-1-carboxamide

HRID 2410883Notes

Reaction equation

HRID 2410883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:28]([NH2:30])=[O:29])[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][O:25][CH2:24][CH2:23]2)[CH:15]=4)[CH:5]=[CH:6][C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[Br:37][CH2:38][CH2:39]Br.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.CN(C=O)C>[Br:37][CH2:38][CH2:39][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:10]=[C:11]([C:28]([NH2:30])=[O:29])[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][O:25][CH2:24][CH2:23]2)[CH:15]=4)=[CH:3][C:2]=1[Cl:1]

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 666057543-(3-chloro-4-hydroxyphenyl)-7-morpholino-9H-carbazole-1-carboxamide

Product 1

HCID 666050533-(4-(2-bromoethoxy)-3-chlorophenyl)-7-morpholino-9H-carbazole-1-carboxamideYield 91.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 100 ml round bottom flask was loaded with 3-(3-chloro-4-hydroxyphenyl)-7-morpholino-9H-carbazole-1-carboxamide (114.9 mg, 0.245 mmol, Example 406), K2CO3 (386 mg, 2.79 mmol), DMF (10 ml) and 1,2-dibromoethane (0.24 ml, 2.79 mmol) and the mixture stirred at room temperature for 4 hours. The reaction mixture was partitioned between 500 ml water+citric acid (0.5 M solution in water) (20 ml, 10.00 mmol) and 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 118.6 mg 3-(4-(2-bromoethoxy)-3-chlorophenyl)-7-morpholino-9H-carbazole-1-carboxamide. MS (ESI) m/e+=528/530/532, m/e−=526/528/530 consistent with isotope pattern for 1 Br and 1 Cl. 1H NMR (DMSO-d6) δ ppm 11.14 (s, 1H), 8.50 (d, 1H, J=1.5), 8.34 (b, 1H), 8.15 (d, 1H, J=1.6), 8.07 (d, 1H, J=8.5), 8.01 (d, 1H, J=2.2), 7.83 (dd, 1H, J=8.6, 2.4), 7.52 (b, 1H), 7.31 (d, 1H, J=8.8), 7.24 (d, 1H, J=2.0), 6.95 (dd, 1H, J=8.8, 2.2), 4.50 (t, 2H, J=5.5),), 3.89 (t, 2H, J=5.5), 3.83-3.79 (m, 4H), 3.22-3.17 (m, 4H).

Workup

  1. washThe organic layer was washed
  2. additionwith dilute (1+5) aq. NaHCO3 solution
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-df47cbeb35884b199fa7c381f3b8534d
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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