Dichloromethane → 9-Bromo-2-[2-(2-chloro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene

HRID 2044285Notes

Reaction equation

HRID 2044285 reaction equation
BrC1C=CC2C3C(CCOC=2C=1)=CN(C1N(C2C=CC(F)=CC=2F)N=CN=1)N=3.Cl[C:30]1[N:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[Cl:41])[N:33]=[CH:32][N:31]=1.[Br:42][C:43]1[CH:44]=[CH:45][C:46]2[O:55][CH2:54][CH2:53][C:52]3[C:48](=[N:49][NH:50][CH:51]=3)[C:47]=2[CH:56]=1.C(Cl)Cl>C1CCCCC1>[Br:42][C:43]1[CH:44]=[CH:45][C:46]2[O:55][CH2:54][CH2:53][C:52]3[C:48](=[N:49][N:50]([C:30]4[N:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[Cl:41])[N:33]=[CH:32][N:31]=4)[CH:51]=3)[C:47]=2[CH:56]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 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 582044415-Chloro-1-(2-chloro-phenyl)-1H-[1,2,4]triazoleHCID 178419296HCID 178419296, compound

Product 1

HCID 582043869-Bromo-2-[2-(2-chloro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azuleneYield 42%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

9-Bromo-2-[2-(2-chloro-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-chloro-phenyl)-1H-[1,2,4]triazole (2.25 g, 10.5 mmol) and 9-bromo-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene (1.9 g, 7 mmol), the crude product was subjected to flash chromatography (SiO2, gradient 0 to 60% DCM (+10% ethyl acetate) in cyclohexane) to give 9-Bromo-2-[2-(2-chloro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulene (1.3 g, 33%). LCMS RT=4.82 M+H+=442/444

Sources & evidence

ORD record
ord-0e5aa508492c456ebd0a8ca380ba3796
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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