Sodium Hydroxide → HCID 2757432, compound

HRID 1016640Notes

Reaction equation

[Cl-:1].Cl[CH:3]=[N+](C)C.Cl[C:8]1[CH:9]=[CH:10][C:11]2[N:12]([CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:16]=2)[CH:13]=1.[OH-:24].[Na+]>CN(C)C=O>[Cl:1][C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]([CH:3]=[O:24])=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[N:16]=2)[CH:13]=1

Participants

Conditions

Temperature: 75 °C

Procedure

N-(Chloromethylene)-N-methylmethanaminium chloride (1.17 g, 9.1 mmol) was added to a solution of 6-chloro-2-(4-chlorophenyl)imidazo[1,2-a]pyridine (Description 17, 0.8 g, 3.0 mmol) in dimethylformamide (50 mL) and the mixture was stirred at 75° C. overnight. The mixture was cooled and poured onto a mixture of ice (500 g) and aqueous sodium hydroxide (2M, 500 mL). The solid was collected, dissolved in dichloromethane, washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with ether and the solid was collected and dried in vacuo to give the title compound as a colorless solid (0.7 g, 79%). 1H NMR (360 MHz, CDCl3) δ 10.06 (1H, s), 9.75 (1H, d, J 1.8 Hz), 7.77 (2H, d, J 8.5 Hz), 7.75 (1H, d, J 9.4 Hz), 7.53 (2H, d, J 8.5 Hz), and 7.56 (1H, dd, J 9.4, 1.8 Hz). m/z (ES+) 291, 293 (M+1).

Workup

temperatureThe mixture was cooled
customThe solid was collected
dissolutiondissolved in dichloromethane
washwashed with brine
dry with materialdried (MgSO4)
customthe solvent was evaporated under reduced pressure
customThe residue was triturated with ether
customthe solid was collected
customdried in vacuo

Sources & evidence

ORD record: ord-f8b9fe652e494e52a570d3061f106b7d
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476045B2

Reaction notes

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