Sodium Carbonate → HCID 86679167, compound

HRID 1774813Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O-:13])=[O:12])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[K+].[CH3:15][N:16]1[C:25]2[C:20](=[CH:21][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:23][CH:24]=2)[CH2:19][CH2:18][C:17]1=[O:35].C([O-])([O-])=O.[Na+].[Na+]>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.CN(C=O)C>[CH3:15][N:16]1[C:25]2[C:20](=[CH:21][C:22]([C:2]3[CH:3]=[C:4]([C:8]4([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]4)[CH:5]=[N:6][CH:7]=3)=[CH:23][CH:24]=2)[CH2:19][CH2:18][C:17]1=[O:35]

Participants

Conditions

Temperature: 120 °C

Procedure

A flask was charged with potassium 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate (0.5 g, 1.52 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, 0.479 g, 1.67 mmol) and DMF (7 mL). Then, bis(triphenylphosphine)palladium(II)chloride (0.106 g, 0.152 mmol), followed by 1N aqueous Na2CO3 solution (3.64 mL, 2.4 mmol) were added and the reaction was heated to 120° C. (pre-heated oil bath) for 1 h. The mixture was evaporated to dryness and the residue purified by silica gel flash chromatography eluting with a 0 to 15% MeOH-DCM gradient to give the title compound (0.551 g, 100%) as a brown solid. MS: 323.4 (M+H+).

Workup

additionwere added
temperature(pre-heated oil bath) for 1 h
customThe mixture was evaporated to dryness
customthe residue purified by silica gel flash chromatography
washeluting with a 0 to 15% MeOH-DCM gradient

Sources & evidence

ORD record: ord-768dfcf5fe884cd4896590056650d50b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

Loading…