1,5-Diazabicyclo(4.3.0)non-5-ene → N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258554Notes

Reaction equation

[OH:1][N:2]=[C:3]([C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1CN2C(=NCCC2)C1.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32]Br)[N:27]=1>CC#N>[Br:25][C:26]1[N:27]=[C:28]([CH2:32][O:1][N:2]=[C:3]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][N:11]=2)[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) stirred solution of N-hydroxy-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (6.47 g, 31.88 mmol, 1.0 eq.) in 250 ml of MeCN, was added dropwise DBN (4.35 g, 35.07 mmol, 1.0 eq.). The reaction was stirred for 5 mins before addition of 2-bromo-6-(bromomethyl)pyridine (8.8 g, 35.07 mmol, 1.1 eq.) portionwise. The mixture was stirred for further 5 mins before removal of the cooling bath and continued at ambient temperature. MeCN was evaporated and the residue was purified by chromatography on silica gel to yield N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (9.4 g, 75% yield, 10:1 mixture of stereoisomers) as a pale yellow oil.

Workup

customcontinued at ambient temperature
customMeCN was evaporated
customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-a232a4a05f6e47e680116786db2e3de8
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466176B2

Reaction notes

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