Hydrochloric Acid → 2-bromo-5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)benzoic acid

HRID 1746431Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:9]([S:12](=[O:27])(=[O:26])[N:13]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH3:25])=[CH:20][CH:19]=2)[CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].C(OCCCC)=C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.Cl>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([S:12](=[O:26])(=[O:27])[N:13]([C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH3:25])=[CH:22][CH:23]=2)[CH2:14][CH:15]([CH3:16])[CH3:17])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of methyl 2-bromo-5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)benzoate (300 mg, 0.660 mmol), palladium(II) acetate (14.82 mg, 0.066 mmol), 1-(vinyloxy)butane (BVE) (0.427 mL, 3.30 mmol) and triphenylphosphine (34.6 mg, 0.132 mmol) in acetonitrile (1 mL) in air, at room temperature, was added triethylamine (0.110 mL, 0.792 mmol). The reaction vessel was sealed and heated by microwaves to 150° C. for 1 hour then the solvent was evaporated in vacuo and the residue redissolved in tetrahydrofuran (THF) (1.0 mL) and treated with HCl (2N, 1 mL, 3.29 mmol). The mixture was stirred vigorously for 1 hour then stood overnight. Analysis showed hydrolysed starting material was present. The crude was purified by MDAP (Method F) to isolate the hydrolysed starting material as the product, 84.8 mg. LCMS (M+1) 440/442, RT 1.25 mins.

Workup

customThe reaction vessel was sealed
customthe solvent was evaporated in vacuo
dissolutionthe residue redissolved in tetrahydrofuran (THF) (1.0 mL)
waitthen stood overnight
customThe crude was purified by MDAP (Method F)
customto isolate the
customLCMS (M+1) 440/442, RT 1.25 mins

Sources & evidence

ORD record: ord-9a66be6d9c174df4b7f3e75cdaf28c28
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150508B2

Reaction notes

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