4-Methoxypyridine → 1-(4-bromobutyryl)-2-(3,4,5-trifluorophenyl)-2,3-dihydro-1H-pyridin-4-one

HRID 553945Notes

Reaction equation

HRID 553945 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Br:9][CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14].[F:16][C:17]1[CH:18]=[C:19]([Mg]Br)[CH:20]=[C:21]([F:24])[C:22]=1[F:23]>>[Br:9][CH2:10][CH2:11][CH2:12][C:13]([N:6]1[CH:7]=[CH:8][C:3](=[O:2])[CH2:4][CH:5]1[C:19]1[CH:18]=[C:17]([F:16])[C:22]([F:23])=[C:21]([F:24])[CH:20]=1)=[O:14]

Participants

4

Reactant 3

HCID 692784-MethoxypyridineHCID 702254-Bromobutyryl chlorideHCID 178505944HCID 178505944, compound

Product 1

HCID 674628841-(4-bromobutyryl)-2-(3,4,5-trifluorophenyl)-2,3-dihydro-1H-pyridin-4-one

Procedure

1.02 g of the title compound was obtained from 4-methoxypyridine (1.52 mL), 3,4,5-trifluorophenylmagnesium bromide (0.3 M solution in THF, 50 mL), and 4-bromobutyryl chloride (1.74 mL) according to the method described in Tetrahedron Letters, 1986, vol. 27, p. 4549-4552. The property values of the compound are as follows.

Sources & evidence

ORD record
ord-399fd2fa196640408c2480ae8de8d97a
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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