Potassium Phosphate, Tribasic → HCID 89647845, compound

HRID 2281014Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8](Br)=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:4].[NH2:16][C@@H:17]([C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1)[CH2:18][N:19]([CH3:32])[S:20]([C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1)(=[O:22])=[O:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:16][C@@H:17]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[CH2:18][N:19]([CH3:32])[S:20]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)(=[O:21])=[O:22])=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A reaction mixture of 5-Bromo-quinoline-8-carboxylic acid methyl ester (600.00 mg; 2.25 mmol; 1.00 eq.), N—[(S)-2-Amino-2-(3-fluoro-phenyl)-ethyl]-N-methyl-4-nitro-benzenesulfonamide (876.48 mg; 2.48 mmol; 1.10 eq.), potassium phosphate, tribasic (957.26 mg; 4.51 mmol; 2.00 eq.), dicyclohexyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (214.99 mg; 0.45 mmol; 0.20 eq.), palladium (+2) acetate (50.62 mg; 0.23 mmol; 0.10 eq.) and toluene (5 ml) in microwave tube were stirred at 100° C. overnight. The crude was purified by prep HPLC (Basic condition) to afford (S)-5-{1-(3-Fluoro-phenyl)-2-[methyl-(4-nitro-benzenesulfonyl)-amino]-ethylamino}-quinoline-8-carboxylic acid methyl ester (250 mg). LC-MS (M+H=339, obsd.=339).

Workup

customThe crude was purified by prep HPLC (Basic condition)

Sources & evidence

ORD record: ord-2c0c8c888fde49aabcd2566bc3828294
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139568B2

Reaction notes

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