Pyridine → 6-(4-bromophenyl)-5H-thieno[3,2-c]pyridin-4-one

HRID 1814497Notes

Reaction equation

HRID 1814497 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12](N3CCN(CC)CC3)[C:11]3[CH:22]=[CH:23][S:24][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.C(N(CC)CC)C.CC([OH:62])(C#C)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:62])[C:11]3[CH:22]=[CH:23][S:24][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 1049PyridineHCID 82582-Methyl-3-butyn-2-olHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 225026376-(4-Bromophenyl)-4-(4-ethylpiperazin-1-yl)thieno[3,2-c]pyridine

Product 1

HCID 225024536-(4-bromophenyl)-5H-thieno[3,2-c]pyridin-4-oneYield 109.5%

Procedure

6-(4-Bromophenyl)-4-(4-ethylpiperazin-1-yl)thieno[3,2-c]pyridine (0.96 g) was heated under reflux in the presence of bistriphenylphosphine dichloride (48 mg), triphenylphosphine (174 mg) and cuprous iodide (46 mg), in 2-methyl-3-butyn-2-ol (0.26 g), pyridine (15 ml) and triethylamine (30 ml) for 1.5 hr. The reaction solution was evaporated, and the resulting residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane system), to give 0.80 g of the title compound as a pale yellow oil.

Workup

  1. customThe reaction solution was evaporated
  2. customthe resulting residue was purified by NH-silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-aa5cb38b91e546c1a84ada7b81137dd2
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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