Ethyl Acetate → 9-bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene

HRID 2044283Notes

Reaction equation

HRID 2044283 reaction equation
Br[C:2]1[CH:28]=[CH:27][C:5]2[C:6]3[C:10]([CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1)=[CH:9][N:8]([C:14]1[N:15]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[N:16]=[CH:17][N:18]=1)[N:7]=3.ClC1N(C2C=CC(F)=CC=2F)N=CN=1.[Br:43]C1C=CC2OCCC3C(=NNC=3)C=2C=1.C(OCC)(=O)C>C1CCCCC1>[Br:43][C:28]1[CH:2]=[CH:3][C:4]2[O:13][CH2:12][CH2:11][C:10]3[C:6](=[N:7][N:8]([C:14]4[N:15]([C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=5[F:26])[N:16]=[CH:17][N:18]=4)[CH:9]=3)[C:5]=2[CH:27]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 513479048-bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azuleneHCID 582049865-chloro-1-(2,4-difluoro-phenyl)-1H-[1,2,4]triazoleHCID 178419296HCID 178419296, compound

Product 1

HCID 582044889-bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azuleneYield 62%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

9-Bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene was prepared similarly to 8-bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene from 5-chloro-1-(2,4-difluoro-phenyl)-1H-[1,2,4]triazole (1.33 g, 6.16 mmol) and 9-bromo-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene (1.36 g, 5.13 mmol), the crude product was subjected to flash chromatography (SiO2, gradient 0 to 35% ethyl acetate in cyclohexane) to give 9-Bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen (1.42 g, 62%). LCMS RT=4.80 M+H+=444/446.

Sources & evidence

ORD record
ord-2be31a6072524ec8ac4f84c2bd08db63
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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