Dimethylformamide → HCID 86679181, compound

HRID 1774829Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1.[CH3:10][N:11]1[C:20]2[C:15](=[CH:16][C:17](B3OC(C)(C)C(C)(C)O3)=[CH:18][CH:19]=2)[CH2:14][CH2:13][C:12]1=[O:30].CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[OH:9][CH2:8][C:4]1[CH:3]=[C:2]([C:17]2[CH:16]=[C:15]3[C:20](=[CH:19][CH:18]=2)[N:11]([CH3:10])[C:12](=[O:30])[CH2:13][CH2:14]3)[CH:7]=[N:6][CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A microwave vial was charged with (5-bromo-pyridin-3-yl)-methanol (376 mg, 2.0 mmol), 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) (574 mg, 2.0 mmol) and DMF (4 mL). After purging the reaction mixture with argon, bis(triphenylphosphine)palladium(II)chloride (140 mg, 0.2 mmol) and 2 N aq. Na2CO3 solution (2.0 mL, 4 mmol) were added and the reaction was heated in the microwave at 120° C. for 50 min. The reaction mixture was diluted with EtOAc, filtered through Dicalite and washed with EtOAc (2×20 mL). The resulting filtrate was washed with brine, dried over anhydrous Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (198 mg, 74%) as a white solid. MS: 269.2 (M+H+).

Workup

additionwere added
filtrationfiltered through Dicalite
washwashed with EtOAc (2×20 mL)
washThe resulting filtrate was washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
customevaporated to dryness
customThe residue was purified by silica gel flash chromatography
washeluting with a 0 to 5% MeOH-DCM gradient

Sources & evidence

ORD record: ord-87b222b5dc1649eda44b8f7d3137d694
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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