1-Bromopropane → HCID 15342497, compound

HRID 440312Notes

Reaction equation

HRID 440312 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[S:10][CH:9]=2)=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:20][CH2:21][CH3:22]>CN(C)C=O>[CH2:20]([N:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[C:8]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH:15]=2)[S:10][CH:9]=1)[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 15342496HCID 15342496, compound

Product 1

HCID 15342497HCID 15342497, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Pyridinylamino)thieno[2,3-c]pyridine (4 g) was added portionwise as a powder to a suspension of sodium hydride (60% oil dispersion, 0.8 g washed with heptane) in 50 mL of dimethylformamide. After anion formation was completed 1-bromopropane (2.2 g) was added. After stirring one hour the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with water saturated sodium chloride, and then was dried (anhydrous magnesium sulfate), filtered and evaporated to 5 g of a dark oil. Elution through silica with 5% methanol in ethyl acetate via flash column chromatography afforded 3.5 g of a yellow solid. Elution through alumina with ether via column chromatography afforded 2.8 g of a yellow solid. Recrystallization from heptane afforded 2.6 g (54.8%) of yellowish crystals, m.p. 119°-120° C.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water saturated sodium chloride
  5. dry with materialwas dried (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated to 5 g of a dark oil
  8. washElution through silica with 5% methanol in ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-1672f69855004ec4b27452fc7aa0f32f
Source dataset
uspto-grants-1996_05
Patent number
US05519032

Reaction notes

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