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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 1799889
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인쇄 미리보기

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HRID 1799889 반응식
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
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참가 물질

6

반응물 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, 화합물

생성물 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]azulene
수율 62%

시약·촉매·용매 1

HCID 8078Cyclohexane용매

실험 절차

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.

출처 및 근거

ORD 기록
ord-6a73fa86f01f42f5808335a01fcb166f
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08343955B2

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