Sodium Carbonate → HCID 57556174, compound

HRID 2074500Notes

Reaction equation

HRID 2074500 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.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=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>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=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 27343542-Fluorophenylboronic acid

Product 1

HCID 57556174HCID 57556174, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Prepared according to Procedure A using 2-chloro-8-methylquinoline 3-carbaldehyde (1.0 g, 4.86 mmol), 2-fluorophenyl boronic acid (0.749 g, 5.35 mmol, 1.1 eq), tetrakis(triphenylphosphine)palladium (0.281 g, 0.24 mmol, 0.05 eq), and sodium carbonate (2.58 g, 24 mmol, 5 eq) in acetonitrile (36 mL) and water (12 mL). After purification, 2-(2-fluorophenyl)-8-methylquinoline-3-carbaldehyde was obtained as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 10.03 (1 H, d, J=3.5 Hz), 8.99 (1 H, s), 8.12 (1 H, d, J=7.8 Hz), 7.85 (1 H, d, J=7.0 Hz), 7.76 (1 H, td, J=7.5, 1.8 Hz), 7.58-7.70 (2 H, m), 7.45 (2 H, td, J=7.5, 1.0 Hz), 7.38 (2 H, td, J=9.4, 1.2 Hz), 2.75 (3 H, s) Mass Spectrum (ESI) m/e=266.0 (M+1)

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-00532ec5cfe34125a74f7fa1089a018b
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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