1-Hexanol → N-{[6-(hexyloxy)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258569Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:24]([OH:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C([O-])([O-])=O.[Cs+].[Cs+].C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:24]([O:30][C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0536 mmol, 1 eq.) in 3 ml of toluene were added hexanol (0.071 g, 0.697 mmol, 1.3 eq.), Cs2CO3 (0.227 g, 0.697 mmol, 1.3 eq.), Pd(OAc)2 (0.002 g, 0.011 mmol, 0.02 eq.) and 2-(Di-t-butylphosphino)-1,1′-binapthyl (0.005 g, 0.013 mmol, 0.025 eq.). The vessel was purged with argon and sealed. The reaction was heated in microwave at 150° C. for 600 s (abs-normal fixed-hold) and diluted with 50 ml of EtOAc, filtered through a “celite” pad. The filtrate was evaporated and the residue was purified by chromatography on silica gel to give N-{[6-(hexyloxy)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.04 g, 17% yield) as a viscous pale brown oil.

Workup

customThe vessel was purged with argon
customsealed
additiondiluted with 50 ml of EtOAc
filtrationfiltered through a “celite” pad
customThe filtrate was evaporated
customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-8c4b24cb99264afba5a24e386f299b41
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466176B2

Reaction notes

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