Sodium hydride → HCID 19347982, compound

HRID 1637188Notes

Reaction equation

HRID 1637188 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]1[CH:15]=[CH:16][C:17]2[C:21]([Cl:22])=[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:19][C:18]=2[CH:28]=1>CN(C)C=O>[Cl:22][C:21]1[C:17]2[CH:16]=[CH:15][C:14]([CH2:13][N:3]3[C:4]4[CH:5]=[N:6][CH:7]=[CH:8][C:9]=4[N:1]=[CH:2]3)=[CH:28][C:18]=2[S:19][C:20]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19347979HCID 19347979, compoundHCID 178419860HCID 178419860, compound

Product 1

HCID 19347982HCID 19347982, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-Imidazo[4,5-c]pyridine (536 mg, 4.5 mmol) was added in portions to a stirred suspension of sodium hydride (144 mg of 60% dispersion in mineral oil, 3.6 mmol) in anhydrous dimethylformamide (5 ml) at 0° C., under a nitrogen atmosphere. After 40 minutes, ethyl 6-bromomethyl-3-chlorobenzo[b]thiophene-2-carboxylate (Preparation 10, 1 g, 3 mmol) was added. After 20 hours the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with more water, dried (magnesium sulfate), and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using 5% methanol in dichloromethane as eluant The fractions containing the less polar product (first isomer eluted from the chromatography column) were evaporated under reduced pressure to give the title compound as a colourless solid (160 mg).

Workup

  1. customAfter 20 hours the mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with more water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel using 5% methanol in dichloromethane as eluant The fractions
  7. additioncontaining the less polar product (first isomer
  8. washeluted from the chromatography column)
  9. customwere evaporated under reduced pressure

Sources & evidence

ORD record
ord-31aa599f04554e2fad1606b627c12ca6
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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