Potassium Acetate → HCID 59370283, compound

HRID 705099Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:8]=[C:7](I)[CH:6]=1)[CH3:2].[CH:20]([C:23]1[N:24]=[N:25][S:26][CH:27]=1)([CH3:22])[CH3:21].C([O-])(=O)C.[K+]>CN(C=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][N:12]=2)[CH:8]=[C:7]([C:27]2[S:26][N:25]=[N:24][C:23]=2[CH:20]([CH3:22])[CH3:21])[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 3-iodo-5-(5-methyl-pyridin-2-yl)-benzoic acid ethyl ester (367 mg, 1 mmol), 4-isopropyl-[1,2,3]thiadiazole (640 mg, 5 mmol), palladium II tetrakis(triphenylphosphine) (35 mg, 0.03 mmol) and potassium acetate (196 mg, 2 mmol) in 10 mL of DMF was warmed to 120° C. and stirred for 16 hours. The reaction mixture was cooled and transferred directly onto a silica column and purified by liquid chromatography (0% to 10% EtOAc/hexanes) to give 250 mg of 3-(4-isopropyl-[1,2,3]thiadiazol-5-yl)-5-(5-methyl-pyridin-2-yl)-benzoic acid ethyl ester, MS (M+H)=368.

Workup

temperatureThe reaction mixture was cooled
custompurified by liquid chromatography (0% to 10% EtOAc/hexanes)

Sources & evidence

ORD record: ord-a8489002d1a0470dbd9265aece495e53
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09173861B2

Reaction notes

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