Sodium Carbonate → 2-Furan-2-yl-6-(4-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

HRID 2242891노트

반응식

HRID 2242891 반응식
Br[C:2]1[N:3]=[C:4]([NH2:16])[C:5]2[N:6]([N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH:7]=1.[F:17][C:18]([F:29])([F:28])[C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:9]1[N:10]=[C:5]2[C:4]([NH2:16])=[N:3][C:2]([C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:29])([F:28])[F:17])=[CH:20][CH:21]=3)=[CH:7][N:6]2[N:8]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 71401630[1,2,4]Triazolo[1,5-a]pyrazin-8-amine, 6-bromo-2-(2-furanyl)-

생성물 1

HCID 112332482-Furan-2-yl-6-(4-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 6-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamine (50 mg, 0.179; see Examples 1 and 2), 4-trifluoromethyl-phenyl boronic acid (0.196 mmol), Pd(dppf)Cl2 (7 mg, 0.009 mmol), and aqueous Na2CO3 (2 M, 330 μL) in DMF (2 mL) was degassed under N2 and then heated (at around 100° C.) for overnight. The reaction was filtered and then purified by HPLC (C18, H2O:MeCN gradient). 1H NMR (300 MHz, DMSO-d6) δ 6.77 (dd, J=3.4, 1.8 Hz, 1H), 7.19 (dd, J=3.4, 0.8 Hz, 1H), 7.70 (br. s, 2H), 7.87 (d, J=8.2 Hz, 2H), 7.93 (dd, J=1.8, 0.7 Hz, 1H), 8.31 (d, J=8.2 Hz, 2H), 8.8 (s, 1H). MS: m/z 346 [M+H]+.

후처리

  1. customwas degassed under N2
  2. filtrationThe reaction was filtered
  3. custompurified by HPLC (C18, H2O:MeCN gradient)

출처 및 근거

ORD 기록
ord-89d1c4b68dea468eb13399318bdd4df4
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674791B2

반응 노트

불러오는 중…