Sodium Carbonate → HCID 57707958, compound

HRID 216753Notes

Reaction equation

HRID 216753 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O.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>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 6890822-Chloro-8-methylquinoline-3-carboxaldehydeHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 57707958HCID 57707958, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Prepared according to Procedure A using 2-chloro-8-methylquinoline 3-carbaldehyde (0.206 g, 1 mmol), 2-methoxyphenyl boronic acid (0.167 g, 1.1 mmol, 1.1 eq), tetrakis(triphenylphosphine)palladium (0.058 g, 0.05 mmol, 0.05 eq), and sodium carbonate (0.530 g, 5 mmol, 5 eq) in acetonitrile (7.5 mL) and water (2.5 mL). After purification, 2-(2-methoxyphenyl)-8-methylquinoline-3-carbaldehyde (0.250 g, 90%) was obtained as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.86 (1H, s), 8.88 (1H, s), 8.13 (1H, d, J=8.1 Hz), 7.85 (1H, d, J=7.1 Hz), 7.56-7.74 (3H, m), 7.22-7.30 (2H, m), 3.78 (3H, s), 2.80 (3H, s) Mass Spectrum (ESI) m/e=278.0 (M+1)

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-a6664a9a25214f55bf7a77b61fcca8e2
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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