Dimethylformamide → ethyl 2-{9-[3-methoxy-4-((5-methyl-2-phenyl-oxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}acetate

HRID 2194298Notes

Reaction equation

HRID 2194298 reaction equation
[H-].[Na+].CN(C)C=O.[CH:8]1[C:20]2[NH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=2[C:11]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:10][CH:9]=1.Cl[CH2:29][C:30]1[CH:49]=[CH:48][C:33]([O:34][CH2:35][C:36]2[N:37]=[C:38]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[O:39][C:40]=2[CH3:41])=[C:32]([O:50][CH3:51])[CH:31]=1>O>[CH3:51][O:50][C:32]1[CH:31]=[C:30]([CH:49]=[CH:48][C:33]=1[O:34][CH2:35][C:36]1[N:37]=[C:38]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:39][C:40]=1[CH3:41])[CH2:29][N:19]1[C:20]2[CH:8]=[CH:9][CH:10]=[C:11]([O:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:12]=2[C:13]2[C:18]1=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 223446094-(4-Chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 58489982ethyl 2-(9H-carbazole-4-yloxy)acetate

Product 1

HCID 59571731ethyl 2-{9-[3-methoxy-4-((5-methyl-2-phenyl-oxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18 mg of sodium hydride (60%) was added to N,N-dimethylformamide (5 mL) solution of 107 mg of ethyl 2-(9H-carbazole-4-yloxy)acetate, and stirred at room temperature for 20 minutes. Thereafter, 144 mg of 4-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-5-methyl-2-phenyloxazole was added thereto, and stirred at room temperature for 1 hour. The reaction mixture was poured into water, and extracted twice with ethyl acetate. The combined extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the residue was crystallized from methanol, isolated by filtration, and washed with methanol. The residue was dried under reduced pressure, and 107 mg of the subject compound was prepared as white crystal.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. extractionextracted twice with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customthe residue was crystallized from methanol
  9. customisolated by filtration
  10. washwashed with methanol
  11. dry with materialThe residue was dried under reduced pressure, and 107 mg of the subject compound
  12. customwas prepared as white crystal

Sources & evidence

ORD record
ord-22a837fb8cca479fad41e9821d9b9d12
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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