Dimethylformamide → HCID 86647506, compound

HRID 2194314Notes

Reaction equation

HRID 2194314 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH3:25][C:26]1[O:30][C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:28][C:27]=1[CH2:37][O:38][C:39]1[CH:59]=[CH:58][C:42]([CH2:43][N:44]2[C:56]3[CH:55]=[CH:54][CH:53]=[C:52]([OH:57])[C:51]=3[C:50]3[C:45]2=[CH:46][CH:47]=[CH:48][CH:49]=3)=[CH:41][C:40]=1[O:60][CH3:61]>C(O)C.O>[CH3:61][O:60][C:40]1[CH:41]=[C:42]([CH:58]=[CH:59][C:39]=1[O:38][CH2:37][C:27]1[N:28]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:30][C:26]=1[CH3:25])[CH2:43][N:44]1[C:56]2[CH:55]=[CH:54][CH:53]=[C:52]([O:57][CH:2]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:51]=2[C:50]2[C:45]1=[CH:46][CH:47]=[CH:48][CH:49]=2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 97780Ethyl bromophenylacetateHCID 59571732HCID 59571732, compound

Product 1

HCID 86647506HCID 86647506, compoundYield 180.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

5.26 g of ethyl α-bromophenylacetate and 4.23 g of potassium carbonate (powder) were added to N,N-dimethylformamide (50 mL) suspension of 10.0 g of 9-{4-[(5-methyl-2-phenyloxazole-4-yl)methoxy]-3-methoxybenzyl}-9H-carbazole-4-ol, and stirred at 60° C. for 2 hours. After the reaction mixture was allowed to cool, water and ethanol were added, the crystalline precipitate was isolated by filtration, and 24 g of ethyl (±)-2-{9-[3-methoxy-4-((5-methyl-2-phenyl-oxazole-4-yl)methoxy)-benzyl]-9H-carbazole-4-yloxy}-2-phenylacetate (undried) was prepared. This was dissolved in mixture of ethanol-tetrahydrofuran, 4.1 mL of 5 N sodium hydroxide solution was added and stirred at 60° C. for 1 hour. The reaction mixture was allowed to cool, and then adjusted to pH3 with 1 N hydrochloric acid, the crystalline precipitate was isolated by filtration, washed with ethyl acetate, dried under reduced pressure, and 10.6 g of the subject compound was prepared as white crystal.

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-d66835d26b7f4ed7b9f071a4b8e768a6
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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