Ethyl 2-azido-7-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]hept-6-ynoate → Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine-7-carboxylate

HRID 71212Notes

Reaction equation

[N:1]([CH:4]([CH2:10][CH2:11][CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[O:25][C:24]([CH3:26])=[N:23][CH:22]=2)=[C:17]([O:27][CH3:28])[CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3]>ClC1C=CC=CC=1>[CH3:28][O:27][C:17]1[CH:16]=[C:15]([C:14]2[N:3]=[N:2][N:1]3[CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11][CH2:12][C:13]=23)[CH:20]=[CH:19][C:18]=1[C:21]1[O:25][C:24]([CH3:26])=[N:23][CH:22]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of ethyl 2-azido-7-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]hept-6-ynoate (1.40 g) in chlorobenzene (28 mL) was stirred at 110° C. for 4 hr. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.34 g).

Workup

customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-6fd409b2b3e749a49d159ed156934c72
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822699B2

Reaction notes

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