Water → HCID 67138479, compound

HRID 2194311Notes

Reaction equation

HRID 2194311 reaction equation
BrC[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19]N(C)C=O.[CH3:24][C:25]1O[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:27][C:26]=1[CH2:36][O:37][C:38]1[CH:58]=[CH:57][C:41]([CH2:42][N:43]2[C:55]3[CH:54]=[CH:53][CH:52]=[C:51](O)[C:50]=3[C:49]3[C:44]2=[CH:45][CH:46]=[CH:47][CH:48]=3)=[CH:40][C:39]=1[O:59][CH3:60].[OH2:61]>>[CH3:24][C:25]1[O:61][C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[N:27][C:26]=1[CH2:36][O:37][C:38]1[CH:58]=[CH:57][C:41]([CH2:42][N:43]2[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:49]=3[C:50]3[C:55]2=[CH:54][CH:53]=[CH:52][C:51]=3[O:16][CH2:13][C:11]2[CH:12]=[CH:3][C:4]([C:5]([O:7][CH2:8][CH3:19])=[O:6])=[CH:9][CH:10]=2)=[CH:40][C:39]=1[O:59][CH3:60]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 59571732HCID 59571732, compound

Product 1

HCID 67138479HCID 67138479, compound

Conditions

Temperature
90 °C

Procedure

47 mg of methyl 2-bromomethylbenzoate and 27 mg of potassium carbonate (powder) were added to N,N-dimethylformamide (2 mL) solution of 98 mg of 9-{4-[(5-methyl-2-phenyloxazole-4-yl)methoxy]-3-methoxybenzyl}-9H-carbazole-4-o 1, and stirred at 90° C. for 1 hour. After the reaction mixture was allowed to cool, water was added thereto, and then extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the residue was crystallized from a small amount of ethanol, isolated by filtration with n-hexane, dried under a reduced pressure, and 110 mg of the subject compound was prepared.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was crystallized from a small amount of ethanol
  8. customisolated by filtration with n-hexane
  9. dry with materialdried under a reduced pressure, and 110 mg of the subject compound
  10. customwas prepared

Sources & evidence

ORD record
ord-8cb8cbd342e44d839e2d0839295afb53
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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