Cesium carbonate → HCID 56656122, compound

HRID 882194Notes

Reaction equation

HRID 882194 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:23]=[CH:22][C:11]2[N:12]([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:13](=[O:16])[N:14]([CH3:15])[C:10]=2[CH:9]=1.[OH:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1>O.C1COCC1>[CH3:19][C:18]([CH3:21])([CH3:20])[CH2:17][N:12]1[C:11]2[CH:22]=[CH:23][C:8]([C:29]3[CH:28]=[CH:27][CH:26]=[C:25]([OH:24])[CH:30]=3)=[CH:9][C:10]=2[N:14]([CH3:15])[C:13]1=[O:16]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 66749106HCID 66749106, compound

Product 1

HCID 56656122HCID 56656122, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Cesium carbonate (3.66 g, 11.2 mmol, 3.0 eq) in Water (1 ml) was charged with a solution of 5-bromo-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1-5, 1.37 g, 3.74 mmol) dissolved in anhydrous THF (19 ml). 3-Hydroxyphenyl boronic acid was introduced and the solution was deoxygenated. The 1,1′-Bis(diphenylphosphino) ferrocene-palladium(II)dichloride dichloromethane complex (153 mg, 0.19 mmol, 0.05 eq) was introduced and the mixture was irradiated in a microwave at 125 deg C. for 15 min. LC/MS analysis showed ˜50% conversion, so more of each reagent was added and the reaction was irradiated again at 120 deg C. for 30 min. The completed reaction was partitioned between EtOAc (2×25 ml) and saturated aqueous NaHCO3 (25 ml), and the combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified via flash column chromatography (SiO2: 100% Hex to 60:40 EtOAc/Hex), affording 1-(2,2-dimethylpropyl)-5-(3-hydroxyphenyl)-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (1479) as a pink-orange solid. 1H NMR (500 MHz, CDCl3) δ 7.34-7.29 (m, 2H), 7.21-7.15 (m, 2H), 7.11-7.06 (m, 2H), 6.81 (d, 1H, J=5.4 Hz), 3.68 (s, 2H), 3.47 (s, 3H), 1.07 (s, 9H). LRMS m/z: Calc'd for C19H22N2O2 (M+H) 311.4, found 311.1.

Workup

  1. customthe solution was deoxygenated
  2. additionThe 1,1′-Bis(diphenylphosphino) ferrocene-palladium(II)dichloride dichloromethane complex (153 mg, 0.19 mmol, 0.05 eq) was introduced
  3. customthe mixture was irradiated in a microwave at 125 deg C
  4. additionso more of each reagent was added
  5. customthe reaction was irradiated again at 120 deg C
  6. waitfor 30 min
  7. customThe completed reaction
  8. customwas partitioned between EtOAc (2×25 ml) and saturated aqueous NaHCO3 (25 ml)
  9. dry with materialthe combined organic layers were dried over Na2SO4
  10. concentrationconcentrated
  11. customThe crude product was purified via flash column chromatography (SiO2: 100% Hex to 60:40 EtOAc/Hex)

Sources & evidence

ORD record
ord-0a66c44300df4568b220f6a11400301f
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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