3-(Chloromethyl)pyridine hydrochloride → HCID 54305681, compound

HRID 399071Notes

Reaction equation

[CH3:1][C:2]1([CH3:24])[C:5](=[N:6][OH:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:3]1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.Cl.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Cl)[CH:27]=1>CN(C=O)C.CCOC(C)=O.O>[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:7][N:6]=[C:5]2[C:2]([CH3:24])([CH3:1])[C:3]([C:14]3[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=3)=[C:4]2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of Example 45 (102 mg) in DMF (3 mL) was added Cs2 CO3 (390 mg) and a solution of 3-picolylchloride hydrochloride (154 mg) in DMF (3 mL). The mixture was heated at 80° C. for 18 hr, diluted with EtOAc and H2O. The aqueous phase was extracted with EtOAc, the combined organic phase was washed with brine, dried (MgSO4) and the solvent evaporated. The resulting residue was purified by flash chromatography (silica gel; hexane/EtOAc (40:60)) to give the title compound as white foam; 1H NMR (300 MHz, Ace-d6): δ 1.61 (s,6H), 3.17 (s, 3H), 5.22 (s, 2H), 7.36-7.41 (m, 4H), 7.69 (m, 2H), 7.85 (m, 3H), 7.98 (d, 2H), 8.52 (dd, 1H), 8.68 (br s, 1H).

Workup

extractionThe aqueous phase was extracted with EtOAc
washthe combined organic phase was washed with brine
dry with materialdried (MgSO4)
customthe solvent evaporated
customThe resulting residue was purified by flash chromatography (silica gel; hexane/EtOAc (40:60))

Sources & evidence

ORD record: ord-f171639a70bb4f6ca47e14a6602c613e
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05817700

Reaction notes

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