Triethylamine → HCID 178515928, compound

HRID 632700Notes

Reaction equation

HRID 632700 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 178515928HCID 178515928, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-8be19295bbaf4ff5bef2569a47a0aa2a
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

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