2,5-Difluorobenzenesulfonyl chloride → 1-(2,5-Difluorobenzenesulfonyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 2074613Notes

Reaction equation

HRID 2074613 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:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[S:20]([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:22])=[O:21]

Participants

4

Reactant 2

HCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 578861297-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 578861191-(2,5-Difluorobenzenesulfonyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazineYield 13%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (100 mg) was dissolved in anhydrous pyridine. 2,5-difluorobenzene sulfonyl chloride (1.0 eq) was added and the mixture stirred at room temperature for 16 hours. The reaction mixture was concentrated and purified by column chromatography to give the title compound as a pale yellow solid (13% yield). M.p. 187-188° C., LCMS: m/z=437.73 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.29-3.33 (m, 2H), 3.83 (t, J=4.8 Hz, 2H), 5.08 (bs, 1H), 7.11-7.19 (m, 1H), 7.26-7.33 (m, 1H), 7.58-7.63 (m, 1H), 7.96 (d, J=1.5 Hz, 1H), 8.03 (d, J=1.8 Hz, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-396119f3065841599a0d61951712c8bd
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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