Water → 1,1-Dimethylethyl [2-[3-bromo-5-[(5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-2-benzofuranyl]phenyl]carbamate

HRID 1034439Notes

Reaction equation

HRID 1034439 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:9]=[C:8]2[NH:10][C:11]([CH2:13][CH3:14])=[N:12][C:7]2=[C:6]([CH3:15])[CH:5]=1.[Br:16][C:17]1[C:21]2[CH:22]=[C:23]([CH2:26]Br)[CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38].O>CN(C=O)C>[Br:16][C:17]1[C:21]2[CH:22]=[C:23]([CH2:26][N:10]3[C:8]4=[N:9][C:4]([CH3:3])=[CH:5][C:6]([CH3:15])=[C:7]4[N:12]=[C:11]3[CH2:13][CH3:14])[CH:24]=[CH:25][C:20]=2[O:19][C:18]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 117549251,1-Dimethylethyl [2-[3-bromo-5-(bromomethyl)-2-benzofuranyl]phenyl]carbamateHCID 178437439HCID 178437439, compound

Product 1

HCID 544884991,1-Dimethylethyl [2-[3-bromo-5-[(5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-2-benzofuranyl]phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.2 g) was added in portions over 5 min to a mixture of 5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine (described in EP-A-0400974) (1.0 g) in dry DMF (25 ml) and stirred at room temperature under nitrogen. After 30 min the solution was cooled to 0°-5° C. and 1,1-dimethylethyl [2-[3-bromo-5-(bromomethyl)-2-benzofuranyl]phenyl]carbamate (described in European Patent Specification No. 0 434 249 A, published 26th Jun. 1991) (3.45 g) was added portionwise over 5 min. The mixture was allowed to warm to room temperature and was stirred for 18 h. Water (1 ml) was added and the mixture concentrated in vacuo. Dichloromethane (50 ml) was added and the mixture washed with water (100 ml), dried and concentrated in vacuo. The residue was purified by flash column chromatogrpahy eluting with System D (10:1) to give the title compound (2.0 g) as a colourless foam.

Workup

  1. temperatureAfter 30 min the solution was cooled to 0°-5° C.
  2. addition1991) (3.45 g) was added portionwise over 5 min
  3. temperatureto warm to room temperature
  4. stirringwas stirred for 18 h
  5. concentrationthe mixture concentrated in vacuo
  6. additionDichloromethane (50 ml) was added
  7. washthe mixture washed with water (100 ml)
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatogrpahy
  11. washeluting with System D (10:1)

Sources & evidence

ORD record
ord-4297fadfcfed44b9b9123692523792fc
Source dataset
uspto-grants-1994_05
Patent number
US05317023

Reaction notes

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