Potassium Carbonate → 3-(2-Chloro-5-trifluoromethyl-benzylsulfanylmethyl)-pyrazine-2-carboxylic acid ethyl ester

HRID 1045635Notes

Reaction equation

Br.[CH2:2]([O:4][C:5]([C:7]1[C:12]([CH2:13][S:14][C:15](=N)N)=[N:11][CH:10]=[CH:9][N:8]=1)=[O:6])[CH3:3].[Cl:18][C:19]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:20]=1CBr.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH2:2]([O:4][C:5]([C:7]1[C:12]([CH2:13][S:14][CH2:15][C:20]2[CH:23]=[C:24]([C:27]([F:29])([F:30])[F:28])[CH:25]=[CH:26][C:19]=2[Cl:18])=[N:11][CH:10]=[CH:9][N:8]=1)=[O:6])[CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 3-carbamimidoylsulfanylmethyl-pyrazine-2-carboxylic acid ethyl ester hydrobromide (0.367 g) in acetonitrile (2 ml) was added 2-chloro-5-trifluoromethyl-benzylbromide (commercially available) (0.294 g), potassium carbonate (0.316 g) and water (3 drops). The reaction mixture was heated to 120° C. for 10 minutes in the microwave. The reaction mixture was filtered and the filtrate concentrated. The residue was purified by chromatography on silica gel (eluent: 0-10% v/v ethyl acetate in iso-hexane) to give Compound No. A2 of Table A.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated
customThe residue was purified by chromatography on silica gel (eluent: 0-10% v/v ethyl acetate in iso-hexane)
customto give Compound No

Sources & evidence

ORD record: ord-94eaf54777c0444d8e4724121390778d
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569301B2

Reaction notes

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