1-Bromo-2-Chloroethane → HCID 86718943, compound

HRID 529024Notes

Reaction equation

HRID 529024 reaction equation
[CH2:1]([N:5]([CH2:33][CH2:34][CH2:35][CH3:36])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[NH:11][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:44][CH2:45][Cl:46]>CC#N.O>[Cl:46][CH2:45][CH2:44][N:11]1[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:33][CH2:34][CH2:35][CH3:36])[N:9]=[C:10]1[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24]

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 10796Cesium carbonateHCID 178449065HCID 178449065, compound

Product 1

HCID 86718943HCID 86718943, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (275 mg, 0.56 mmol) in dry MeCN (8.0 mL) was added cesium carbonate (182 mg, 0.56 mmol) and 1-bromo-2-chloroethane (80 mg, 0.56 mmol). The reaction mixture was heated at 50° C. for 10 h, diluted with water and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give the crude product. The crude material was purified by flash chromatography (gradient from 0% to 2% MeOH/CH2Cl2) to provide the title compound (170 mg, 54%). 1H NMR (DMSO-d6) δ 8.46 (d, J=1.6 Hz, 1H), 8.26 (dd, J=8.0, 1.6 Hz, 1H), 7.85 (s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.36-7.33 (m, 3H), 7.27-7.25 (m, 2H), 5.16 (s, 2H), 4.08-4.03 (m, 4H), 3.93 (s, 1.5H), 3.77-3.73 (m, 3.5H), 3.50-3.40 (m, 2H), 1.50-1.45 (m, 4H), 1.35-1.10 (m, 4H), 0.92-0.75 (m, 6H); MS(ESI+) m/z 555.0 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give the crude product
  5. customThe crude material was purified by flash chromatography (gradient from 0% to 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-da613f8e0df44cea8335e1cc61bf85ff
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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