Cesium fluoride → 1-(2-Methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetraz ol-5-one

HRID 628494Notes

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[C:9](Br)=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1.[CH:18]1(B(O)O)[CH2:20][CH2:19]1.[F-].[Cs+]>O1CCOCC1>[CH3:1][O:2][CH2:3][C:4]1[C:9]([CH:18]2[CH2:20][CH2:19]2)=[CH:8][CH:7]=[CH:6][C:5]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-(2-methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 8) 30.1 g, cyclopropylboronic acid 12.9 g, cesium fluoride 46.2 g, [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct 8.2 g and dioxane 680 ml was stirred at 90° C. for four hours. After cooling the reaction mixture, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one 26.0 g.

Workup

temperatureAfter cooling the reaction mixture
filtrationthe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-2400f77e643242598c4322e66dbff0c9
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09314023B2

Reaction notes

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