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Sodium Carbonate → HCID 86679167, compound

HRID 1774813
Notes
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Reaction equation

HRID 1774813 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66788306HCID 66788306, compoundHCID 722082331-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 86679167HCID 86679167, compoundYield 112.5%

Reagents, catalysts & solvents 2

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
Catalyst
HCID 6228DimethylformamideSolvent

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

  1. additionwere added
  2. temperature(pre-heated oil bath) for 1 h
  3. customThe mixture was evaporated to dryness
  4. customthe residue purified by silica gel flash chromatography
  5. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes