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Stannane, tributyl(1-ethoxyethenyl)- → 1-(3-Methyl-2-phenoxyquinolin-8-yl)ethanone

HRID 1055927
Notes
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Reaction equation

HRID 1055927 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([CH3:19])=[CH:7]2.C([Sn](CCCC)(CCCC)[C:25]([O:27]CC)=[CH2:26])CCC>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][C:8]1[C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[C:25](=[O:27])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 897819448-Bromo-3-methyl-2-phenoxyquinoline

Product 1

HCID 897820891-(3-Methyl-2-phenoxyquinolin-8-yl)ethanoneYield 73.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140
Toluene
Solvent

Conditions

Temperature
100 °C

Procedure

A solution of 8-bromo-3-methyl-2-phenoxyquinoline (505.5 mg, 1.609 mmol), tributyl(1-ethoxyvinyl)stannane (Synthonix, Inc., Wake Forest, N.C.; 0.598 mL, 1.770 mmol), and Pd(PPh3)4 (93 mg, 0.080 mmol) in toluene (8.0 mL) was sparged with argon and then stirred under N2 at 100° C. for 16 h. The mixture was cooled to 25° C. and concentrated onto silica gel. Chromatographic purification (silica gel, 0-20% EtOAc/hexanes) furnished 1-(3-methyl-2-phenoxyquinolin-8-yl)ethanone (326.0 mg, 1.176 mmol, 73% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.95 (1H, s), 7.90 (1H, dd, J=7.2, 1.4 Hz), 7.82 (1H, dd, J=8.0, 1.2 Hz), 7.37-7.47 (3H, m), 7.23-7.25 (1H, m), 7.19 (2H, d, J=8.1 Hz), 2.55 (3H, d, J=0.6 Hz), 2.28 (3H, s). m/z (EST, +ve) 278.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to 25° C.
  2. concentrationconcentrated onto silica gel
  3. customChromatographic purification (silica gel, 0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f13d5fd2f3e64449b2541ae4a41463c2
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394297B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes