Diethyl Ether → HCID 59251245, compound

HRID 1466414Notes

Reaction equation

HRID 1466414 reaction equation
C(OC([C:6]1[N:7]=[C:8]([C:19]2[S:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=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)C.[CH3:34][Mg]Br.CC[O:39][CH2:40][CH3:41]>C1COCC1>[Cl:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:18])[C:11]=1[N:9]1[CH:10]=[C:6]([C:40]([OH:39])([CH3:41])[CH3:34])[N:7]=[C:8]1[C:19]1[S:20][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 59251262HCID 59251262, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59251245HCID 59251245, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(2,6-dichlorophenyl)-2-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1H-imidazole-4-carboxylic acid ethyl ester (300 mg, 0.58 mmol) in THF (3 mL) at 0° C. was added a 3.0M solution of methylmagnesium bromide in Et2O (0.80 mL, 2.4 mmol). After addition was completed the flask was removed from the ice-water bath and allowed to warm to ambient temperature. At 40 min the reaction mixture was quenched by addition of satd NH4Cl, extracted with EtOAc, dried (Na2SO4), concentrated and purified by chromatography (silica, EtOAc/Hex, 40:60 to 90:10) to give the title compound (0.17 g, 59%) as a white solid. 1H-NMR (DCM-d2): δ 8.07 (m, 1H), 7.81 (m, 2H), 7.46-7.60 (m, 4H), 7.21 (d, 1H), 6.85 (s, 1H), 6.62 (d, 1H), 3.05 (s, 3H), 2.68 (br s, 1H), 1.61 (s, 6H); MS (ES): 507, 509 [M+H]+.

Workup

  1. additionAfter addition
  2. customwas removed from the ice-water bath
  3. customAt 40 min the reaction mixture was quenched by addition of satd NH4Cl
  4. extractionextracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified by chromatography (silica, EtOAc/Hex, 40:60 to 90:10)

Sources & evidence

ORD record
ord-d5010de953b143a08911f1fa1912e62f
Source dataset
uspto-grants-2015_04
Patent number
US09000022B2

Reaction notes

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