Triethylamine → HCID 178515928, 화합물

HRID 632700노트

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HRID 632700 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 178515928HCID 178515928, 화합물수율 15%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

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. NH4CI. 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, 1 H), 7.43 (d, J=8.59 Hz, 2 H), 7.30 (d, J=8.59 Hz, 2 H), 6.96-7.14 (m, 3 H), 6.74-6.96 (m, 4 H), 6.53-6.74 (m, 3 H), LC/MS (m/z, MH+): 427.3.

후처리

  1. customThe system was flushed with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with DCM and sat. aq. NH4CI
  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)

출처 및 근거

ORD 기록
ord-8be19295bbaf4ff5bef2569a47a0aa2a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321746B2

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