2,5-Difluorobenzoyl chloride → (2,5-difluorophenyl)-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)methanone

HRID 659366Notes

Reaction equation

HRID 659366 reaction equation
[I:1][C:2]1[CH:11]=[N:10][C:5]2[NH:6][CH2:7][CH2:8][NH:9][C:4]=2[CH:3]=1.[F:12][C:13]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:14]=1[C:15](Cl)=[O:16]>>[F:12][C:13]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:14]=1[C:15]([N:9]1[CH2:8][CH2:7][NH:6][C:5]2[N:10]=[CH:11][C:2]([I:1])=[CH:3][C:4]1=2)=[O:16]

Participants

3

Reactant 2

HCID 5880822,5-Difluorobenzoyl chlorideHCID 578861297-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 57885852(2,5-difluorophenyl)-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)methanoneYield 47%

Procedure

7-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (614 mg) was reacted with 2,5-difluorobenzoyl chloride as in General Procedure 2 to give the title compound as an off-white foam (47% yield). M.p. foam, LCMS: m/z=402.20 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.70-1.90 (m, 2H), 3.50-3.65 (m, 2H), 5.29 (bs, 1H), 6.99 (s, 1H), 7.10-7.18 (m, 2H), 7.20-7.25 (m, 1H), 7.99 (s, 1H).

Sources & evidence

ORD record
ord-ee433754ae804c0a93ae470fd682605e
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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