Triethylamine → (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-imidazol-4-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol

HRID 332913ノート

反応式

HRID 332913 の反応式
Br[C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:8]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:9]=3[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:33]([C:35]1[N:36]=[CH:37][N:38]([CH3:40])[CH:39]=1)=[CH2:34]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]2[S:10][C:9]3[CH:19]=[C:20]([OH:23])[CH:21]=[CH:22][C:8]=3[C:7]=2[O:6][C:5]2[CH:24]=[CH:25][C:2](/[CH:34]=[CH:33]/[C:35]3[N:36]=[CH:37][N:38]([CH3:40])[CH:39]=3)=[CH:3][CH:4]=2)=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 120223681H-Imidazole, 4-ethenyl-1-methyl-HCID 867306533-(4-Bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol

生成物 1

HCID 78324876(E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-imidazol-4-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol収率 58.2%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

To a microwave vial, 3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (50 mg, 0.121 mmol) was dissolved in DMF (2 ml) and triethyl amine (0.506 ml, 3.63 mmol). To the solution was added the 4-vinyl-1-methyl imidazole (39.2 mg, 0.363 mmol) and Pd(PPh3)2Cl2 (8.49 mg, 0.012 mmol). The system was flushed with nitrogen and heated at 150° C. for 1 h under microwave radiation. The mixture was cooled to room temperature and diluted with DCM and sat. NH4Cl. The organic layer was collected (phase separator) and purified by reverse phase HPLC (acidic condition, 0.1% TFA in 1-100% CH3CN/H2O) to afford (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-imidazol-4-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol (31 mg, 0.070 mmol, 58.2% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm=3.82 (s, 3H) 6.57-6.74 (m, 3H) 6.75-6.93 (m, 3H) 6.98-7.14 (m, 3H) 7.32-7.54 (m, 5H) 8.73 (s, 1H). LC/MS (m/z, MH+): 441.3.

後処理

  1. customThe system was flushed with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with DCM and sat. NH4Cl
  4. customThe organic layer was collected (phase separator)
  5. custompurified by reverse phase HPLC (acidic condition, 0.1% TFA in 1-100% CH3CN/H2O)

出典と根拠

ORDレコード
ord-71d0f1d59ea7468eb8d3270ff46942c9
出典データセット
uspto-grants-2014_11
特許番号
US08877801B2

反応ノート

読み込み中…