1-Bromo-2,2-dimethylpropane → 1-(2,2-dimethylpropyl)-4-fluoro-5-methoxy-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 882206Notes

Reaction equation

HRID 882206 reaction equation
[F:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].[H-].[Na+].Br[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[CH3:18][C:19]([CH3:22])([CH3:21])[CH2:20][N:10]1[C:6]2[CH:5]=[CH:4][C:3]([O:13][CH3:14])=[C:2]([F:1])[C:7]=2[N:8]([CH3:12])[C:9]1=[O:11]

Participants

5

Reactant 3

HCID 124151-Bromo-2,2-dimethylpropaneHCID 24758Sodium hydrideHCID 866861057-fluoro-6-methoxy-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 667492611-(2,2-dimethylpropyl)-4-fluoro-5-methoxy-3-methyl-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-fluoro-6-methoxy-1-methyl-1,3-dihydro-2H-benzimidazol-2-one (7-4, 250 mg, 1.27 mmol) in anhydrous DMF (1.5 ml) was treated with NaH and 1-Bromo-2,2-dimethylpropane. The reaction was then irradiated in a microwave at 175 deg C. for 25 min. The reaction was partitioned between EtOAc (2×60 ml) and water (75 ml). The combined organic layers were dried over Na2SO4 and concentrated, affording the title compound, 1-(2,2-dimethylpropyl)-4-fluoro-5-methoxy-3-methyl-1,3-dihydro-2H-benzimidazol-2-one (7-5), as an orange oil. 1H NMR (300 MHz, CDCl3) δ 6.65-6.70 (m, 2H), 3.88 (s, 3H), 3.60 (m, 5H), 1.03 (s, 9H). LRMS m/z: Calc'd for C14H19FN2O2(M+H) 267.3, found 267.0.

Workup

  1. customThe reaction was then irradiated in a microwave at 175 deg C
  2. customThe reaction was partitioned between EtOAc (2×60 ml) and water (75 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-af8c0dd53070463da33ddd8d856d1d28
Source dataset
uspto-grants-2015_03
Patent number
US08993779B2

Reaction notes

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