3-Bromopyridine → Tert-butyl 1-(6-methylpyridazin-3-yl)azetidine-3-carboxylate

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:8]1[CH2:11][CH:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]1.[NH:19]1CC(C(NC2C=CC(OC3CCN(C(OC(C)(C)C)=O)CC3)=CC=2)=O)C1>>[CH3:3][C:2]1[N:19]=[N:4][C:5]([N:8]2[CH2:9][CH:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11]2)=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 122863-Bromopyridine

HCID 21828700tert-Butyl azetidine-3-carboxylate

HCID 86702036Tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

Product 1

HCID 86702114Tert-butyl 1-(6-methylpyridazin-3-yl)azetidine-3-carboxylate

Procedure

The title compound was prepared as described in Example 1C, substituting 3-chloro-6-methylpyridazine for 3-bromopyridine and tert-butyl azetidine-3-carboxylate for tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate.

Sources & evidence

ORD record: ord-9667ead9fee54d1a82f9ae008a6bc595
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975398B2

Reaction notes

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