Water → HCID 59251262, compound

HRID 1466413Notes

Reaction equation

HRID 1466413 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[S:20][C:21](Br)=[CH:22][CH:23]=2)[N:9]([C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[CH:10]=1)=[O:5])[CH3:2].[CH3:25][S:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27].C([O-])([O-])=O.[K+].[K+].O>COCCOC>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[S:20][C:21]([C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([S:26]([CH3:25])(=[O:28])=[O:27])[CH:34]=3)=[CH:22][CH:23]=2)[N:9]([C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 59251444HCID 59251444, compound

Product 1

HCID 59251262HCID 59251262, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(5-bromothiophen-2-yl)-1-(2,6-dichlorophenyl)-1H-imidazole-4-carboxylic acid ethyl ester (335 mg, 0.75 mmol), 3-methanesulfonyl-phenylboronic acid (180 mg, 0.90 mmol), K2CO3 (0.32 g, 2.3 mmol), Cl2Pd(dppf)DCM (30 mg, 5 mol %) and H2O (0.4 mL) in DME (4 mL) was sparged with Argon for 5 min and then heated at 80° C. as a sealed flask. After 2 h the reaction mixture was allowed to cool to ambient temperature, filtered (Celite™) and the filter agent rinsed with EtOAc. The combined filtrates were concentrated under reduced pressure and purified by chromatography (silica, EtOAc/Hex, 30:70 to 80:20) to give the title compound (313 mg, 80%) as a pale yellow solid, which was used in the next step without further purification. 1H-NMR (DCM-d2): δ 8.08 (m, 1H), 7.82 (m, 2H), 7.64 (s, 1H), 7.51-7.62 (m, 4H), 7.24 (d, 1H), 6.72 (d, 1H), 438 (q, 2H), 3.05 (s, 3H), 1.40 (t, 3H).

Workup

  1. customwas sparged with Argon for 5 min
  2. temperatureto cool to ambient temperature
  3. filtrationfiltered (Celite™)
  4. washthe filter agent rinsed with EtOAc
  5. concentrationThe combined filtrates were concentrated under reduced pressure
  6. custompurified by chromatography (silica, EtOAc/Hex, 30:70 to 80:20)

Sources & evidence

ORD record
ord-0ce59448cd21425fb280c1635cd5e925
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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