4-Aminopyridine → HCID 9820865, compound

HRID 896096Notes

Reaction equation

[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].[NH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1>CCOCC.C1COCC1>[N:28]1[CH:29]=[CH:30][C:25]([NH:24][C:18](=[O:22])[C:19]([C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:17][CH:16]=3)[CH:8]=2)=[O:20])=[CH:26][CH:27]=1

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of 4.75 g (21.1 mmol) of 1-(4-fluoro-benzyl) indole in 25 ml of ether is added dropwise at 0° C. and under N2 to a solution of 2.25 ml of oxalyl chloride in 25 ml of ether. The mixture is refluxed for 2 hours and the solvent is then evaporated. 50 ml of tetrahydrofuran were [sic] then added to the residue, and the solution is cooled to −5° C. and treated dropwise with a solution of 4.66 g (49.5 mmol) of 4-aminopyridine in 200 ml of THF. The mixture is refluxed for 3 hours and allowed to stand at room temperature overnight. The 4-aminopyridine hydrochloride is filtered off with suction, the precipitate is washed with THF, the filtrate is concentrated in vacuo and the residue is recrystallized from ethyl acetate.

Workup

temperatureThe mixture is refluxed for 2 hours
customthe solvent is then evaporated
additionthen added to the residue
temperatureThe mixture is refluxed for 3 hours
filtrationThe 4-aminopyridine hydrochloride is filtered off with suction
washthe precipitate is washed with THF
concentrationthe filtrate is concentrated in vacuo
customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-219c3eeaa46f4e3592851507c820638f
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919344B2

Reaction notes

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