Triethylamine → HCID 178515928、化合物

HRID 332912ノート

反応式

HRID 332912 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](C(OC(C)(C)C)=O)[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>[NH:38]1[CH:39]=[C:35](/[CH:33]=[CH:34]/[C:2]2[CH:25]=[CH:24][C:5]([O:6][C:7]3[C:8]4[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:9]=4[S:10][C:11]=3[C:12]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=3)=[CH:4][CH:3]=2)[N:36]=[CH:37]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 867306533-(4-Bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-olHCID 86730655tert-butyl 4-vinyl-1H-imidazole-1-carboxylate

生成物 1

HCID 178515928HCID 178515928、化合物収率 15%

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 containing 3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (20 mg, 0.05 mmol) in DMF (2 mL) was added triethyl amine (0.202 mL, 1.45 mmol), tert-butyl 4-vinyl-1H-imidazole-1-carboxylate (28.2 mg, 0.15 mmol) and Pd(PPh3)2Cl2 (3.40 mg, 4.84 μmol). The system was flushed with nitrogen and heated at 150° C. for 1 h under microwave irradiation. The mixture was cooled to room temperature and diluted with DCM and sat. aq. NH4Cl. The organic layer was collected (phase separator), concentrated in vacuo and purified by reverse phase HPLC (basic condition, 0.1% NH4OH in 1-100% CH3CN/H2O) to afford (E)-3-(4-(2-(1H-imidazol-4-yl)vinyl)phenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (3 mg, 7.03 μmol, 15% yield) as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm=7.57 (s, 1H), 7.43 (d, J=8.59 Hz, 2H), 7.30 (d, J=8.59 Hz, 2H), 6.96-7.14 (m, 3H), 6.74-6.96 (m, 4H), 6.53-6.74 (m, 3H). LC/MS (m/z, MH+): 427.3.

後処理

  1. customThe system was flushed with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with DCM and sat. aq. NH4Cl
  4. customThe organic layer was collected (phase separator)
  5. concentrationconcentrated in vacuo
  6. custompurified by reverse phase HPLC (basic condition, 0.1% NH4OH in 1-100% CH3CN/H2O)

出典と根拠

ORDレコード
ord-d2b4f85c0eb640379fea3dc4d9aeb043
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…