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

HRID 2242891ノート

反応式

HRID 2242891 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

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

反応条件

温度
100 °C

実験手順

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]+.

後処理

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

出典と根拠

ORDレコード
ord-89d1c4b68dea468eb13399318bdd4df4
出典データセット
uspto-grants-2010_03
特許番号
US07674791B2

反応ノート

読み込み中…