Hydrochloric Acid → HCID 11578069, compound

HRID 2194313Notes

Reaction equation

HRID 2194313 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[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].Cl>[Cu](I)I.O1CCOCC1>[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][C:2]3[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=3[C:4]([OH:6])=[O:5])[C:51]=2[C:50]2[C:45]1=[CH:46][CH:47]=[CH:48][CH:49]=2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 69402-Bromobenzoic acidHCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 59571732HCID 59571732, compound

Product 1

HCID 11578069HCID 11578069, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

3.53 g of 2-bromobenzoic acid, 2.23 g of copper iodide, 1.63 g of N,N-dimethylglycine hydrochloride, and 15.2 g of cesium carbonate were added to 1,4-dioxane (50 mL) suspension of 5.74 g of 9-{4-[(5-methyl-2-phenyloxazole-4-yl)methoxy]-3-methoxybenzyl}-9H-carbazole-4-ol, and refluxed overnight. 1 N hydrochloric acid was added to the reaction mixture, extracted with ethyl acetate, and washed with brine. The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated in vacuo, the residue was purified by silica gel chromatography (ethyl acetate:n-hexane=2:1), and 1.4 g of the subject compound was prepared as white crystal.

Workup

  1. temperaturerefluxed overnight
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography (ethyl acetate:n-hexane=2:1), and 1.4 g of the subject compound
  8. customwas prepared as white crystal

Sources & evidence

ORD record
ord-2a5276703b24407ca02f620baccc7dde
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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