Ammonium formate → HCID 86697998, compound

HRID 518832Notes

Reaction equation

C[N:2]1[CH:7]([O:8][CH:9]([CH3:11])[CH3:10])[C:6]([N+:12]([O-])=O)=[CH:5][CH:4]=[C:3]1[C:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH:20]=1.[CH:21]([O-])=O.[NH4+]>[Pd].CO>[CH3:21][N:18]1[CH2:19][CH2:20][CH:15]([C:3]2[N:2]=[C:7]([O:8][CH:9]([CH3:10])[CH3:11])[C:6]([NH2:12])=[CH:5][CH:4]=2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a microwave tube, 300 mg of 1-methyl-5-nitro-6-(propan-2-yloxy)-1′,2′,3′,6′-tetrahydro-2,4′-bipyridine are introduced into 22 ml of methanol. 410 mg of ammonium formate and 345 mg of Pd/C (10%) are added. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure, so as to give 288 mg of 6-(1-methylpiperidin-4-yl)-2-(propan-2-yloxy)pyridin-3-amine in the form of a brown gum.

Workup

filtrationThe mixture is filtered on Clarcel
washthe Clarcel is rinsed with methanol
concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record: ord-648dd81ea22b48d08ddb28d5c295355c
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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