Cesium carbonate → HCID 66749484, compound

HRID 882197Notes

Reaction equation

HRID 882197 reaction equation
[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)=[CH:12][C:7]=2[N:6]([CH3:20])[C:5]1=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=1>CN1CCCC1.[Cu]Cl>[CH3:1][C:2]([CH3:23])([CH3:22])[CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]3[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=3)[O:19][C:31]3[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=3)=[CH:12][C:7]=2[N:6]([CH3:20])[C:5]1=[O:21]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 12162Benzonitrile, 4-bromo-HCID 56656122HCID 56656122, compound

Product 1

HCID 66749484HCID 66749484, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 84541-MethylpyrrolidineSolvent

Procedure

A solution of 1-(2,2-dimethylpropyl)-5-(3-hydroxyphenyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-179, 70 mg, 0.23 mmol) and Cesium carbonate (73.5 mg, 0.23 mmol, 1.0 eq) in N-Methylpyrrolidine (1 ml) was stirred at 23 deg C. for 45 min. 4-Bromobenzonitrile and Copper (I) Chloride were added and the resulting mixture was irradiated in a microwave at 150 deg C. for 5 min. LC/MS analysis showed very little conversion, so the reaction was capped and heated in an oil bath at 175 deg C. for 16 h. The resulting crude, dark mixture was run through a filter disk, then purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present), providing 4-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]phenoxy}benzonitrile (4-1) as a tan solid-oil. 1H NMR (400 MHz, CDCl3) δ 7.62 (d, 2H, J=8.7 Hz), 7.48-7.47 (m, 2H), 7.30-7.28 (m, 2H), 7.08 (s, 1H), 7.08-7.02 (m, 4H), 3.69 (s, 2H), 3.47 (s, 3H), 1.06 (s, 9H). LRMS m/z: Calc'd for C26H25N3O2(M+H) 412.5, found 412.3.

Workup

  1. customthe resulting mixture was irradiated in a microwave at 150 deg C
  2. waitfor 5 min
  3. customso the reaction was capped
  4. temperatureheated in an oil bath at 175 deg C
  5. waitfor 16 h
  6. custompurified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present)

Sources & evidence

ORD record
ord-4eed1636f67446e7b6e06a27117308de
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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