Potassium Carbonate → HCID 66749493, compound

HRID 882195Notes

Reaction equation

HRID 882195 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-].[K+].[K+].Cl[C:31]1[C:36]([C:37]#[N:38])=[CH:35][CH:34]=[CH:33][N:32]=1>CS(C)=O>[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[N:32]=[CH:33][CH:34]=[CH:35][C:36]=3[C:37]#[N:38])=[CH:12][C:7]=2[N:6]([CH3:20])[C:5]1=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 810792-ChloronicotinonitrileHCID 56656122HCID 56656122, compound

Product 1

HCID 66749493HCID 66749493, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-(2,2-dimethylpropyl)-5-(3-hydroxyphenyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-179, 23 mg, 0.07 mmol) in DMSO (2 ml) was charged with Potassium carbonate (20.5 mg, 0.15 mmol, 2.0 eq) and 2-Chloro-3-cyanopyridine (15.4 mg, 0.11 mmol, 1.5 eq). The mixture was irradiated in a microwave at 160 deg C. for 20 min. The resulting dark mixture was purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present), providing the title compound, 2-{3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-5-yl]phenoxy} nicotinonitrile (2-1), as a tan solid-oil. 1H NMR (400 MHz, CDCl3) δ 8.34 (d, 1H, J=3.3 Hz), 8.03 (d, 1H, J=5.9 Hz), 7.51-7.50 (m, 2H), 7.42 (s, 1H), 7.32 (d, 1H, J=8.2 Hz), 7.20-7.17 (m, 2H), 7.13-7.09 (m, 2H), 3.70 (s, 2H), 3.49 (s, 3H), 1.06 (s, 9H). LRMS m/z: Calc'd for C25H24N4O2(M+H) 413.4, found 413.2.

Workup

  1. customThe mixture was irradiated in a microwave at 160 deg C
  2. customThe resulting dark mixture was purified via reverse-phase HPLC (Acetonitrile/Water gradient with 0.1% TFA present)

Sources & evidence

ORD record
ord-24b336c9c05143f7b47bd52c6600dbed
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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