Benzyl Bromide → HCID 66818624, compound

HRID 1024786Notes

Reaction equation

HRID 1024786 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([NH:15][C:16]([C:18]2[CH:19]=[C:20]([CH:31]=[C:32]([O:34][C:35]3[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=3)[CH:33]=2)[O:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=2)=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:49](Br)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>CN(C=O)C>[CH2:49]([O:27][C:26](=[O:28])[C:25]1[CH:29]=[CH:30][C:22]([O:21][C:20]2[CH:31]=[C:32]([O:34][C:35]3[CH:36]=[CH:37][C:38]([C:41]#[N:42])=[CH:39][CH:40]=3)[CH:33]=[C:18]([C:16](=[O:17])[NH:15][CH:12]3[CH2:13][CH2:14][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][CH2:11]3)[CH:19]=2)=[CH:23][CH:24]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66818525HCID 66818525, compound

Product 1

HCID 66818624HCID 66818624, compoundYield 0.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.6 g (1.05 mmol) of 4-[3-(4-tert-butoxycarbonylamino-cyclohexylcarbamoyl)-5-(4-cyano-phenoxy)-phenoxy]-benzoic acid was dissolved in 5 ml of DMF. At 0° C. 50 mg (0.35 mmol) of potassium carbonate followed by 45 mg (0.26 mmol) benzylbromide were added and the reaction mixture was stirred for 4 h at RT. Reaction progress was monitored by TLC. Upon completion of the reaction the contents were diluted with 50 ml of ice-water and extracted with 3×50 ml of ethyl acetate, dried over anhydrous sodium sulphate and concentrated under vacuo. Thus obtained crude residue was purified by column chromatography using 60-120 mesh silica-gel and eluted with ethylacetate:hexane (1:9) to give 0.38 mg of the required product. 1H NMR (DMSO-d6): δ 1.25 (4H, m), 1.4 (9H, s), 1.8 (4H, m), 3.18 (1H, m), 3.66 (1H, m), 5.36 (2H, s), 6.76 (1H, d), 7.22 (5H, m), 7.46 (7H, m), 7.88 (2H, d), 8.05 (2H, d), 8.36 (1H, d).

Workup

  1. customAt 0° C
  2. additionwere added
  3. customReaction progress
  4. customUpon completion of the reaction the contents
  5. extractionextracted with 3×50 ml of ethyl acetate
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under vacuo
  8. customThus obtained crude residue
  9. customwas purified by column chromatography
  10. washeluted with ethylacetate:hexane (1:9)

Sources & evidence

ORD record
ord-e4e7abbd2ea7434eaaee2f37fea02b5d
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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