Sodium Carbonate → Ethanesulfonic acid [5-(8-fluoro-1-methyl-2-oxo-1,2-dihydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774889Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH2:8][CH2:7]2.Br[C:24]1[CH:25]=[C:26]([CH2:30][NH:31][S:32]([CH2:35][CH3:36])(=[O:34])=[O:33])[CH:27]=[N:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:24]2[CH:25]=[C:26]([CH2:30][NH:31][S:32]([CH2:35][CH3:36])(=[O:33])=[O:34])[CH:27]=[N:28][CH:29]=2)[CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[C:9](=[O:13])[CH:8]=[CH:7]2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 8-fluoro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (example 208 [E], 20 mg, 0.066 mmol), ethanesulfonic acid (5-bromo-pyridin-3-ylmethyl)-amide (intermediate A-11, 27.4 mg, 0.098 mmol), bis(triphenylphosphine)-palladium(II) chloride (4.6 mg, 0.0066 mmol), and aq. sodium carbonate solution (2 N, 0.07 mL) in DMF (1 mL) was heated in a microwave at 120° C. for 30 minutes. After dilution of the reaction mixture with EtOAc, the organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was then purified by prep-HPLC to afford the title compound (2.5 mg, 10%) as a white solid. MS: 376.3 (M+H+)+.

Workup

washAfter dilution of the reaction mixture with EtOAc, the organic layer was washed with water
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was then purified by prep-HPLC

Sources & evidence

ORD record: ord-555770becf1f4df7afc2c1e5a7b41b31
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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