Sodium Carbonate → 2-(2-Trifluoromethylphenyl)-8-chloroquinoline-3-carbaldehyde

HRID 2074496Notes

Reaction equation

HRID 2074496 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:15][C:16]([F:27])([F:26])[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>[F:15][C:16]([F:27])([F:26])[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]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 149171252,8-Dichloro-quinoline-3-carbaldehyde

Product 1

HCID 575561672-(2-Trifluoromethylphenyl)-8-chloroquinoline-3-carbaldehyde

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Prepared according to Procedure A using 2,8-dichloroquinoline 3-carbaldehyde (1.0 g, 4.42 mmol), 2-trifluoromethylphenyl boronic acid (0.924 g, 4.87 mmol, 1.1 eq), tetrakis(triphenylphosphine)palladium (0.256 g, 0.221 mmol, 0.05 eq), and sodium carbonate (2.34 g, 22.1 mmol, 5 eq) in acetonitrile (30 mL) and water (10 mL). After purification, 2-(2-trifluoromethylphenyl)-8-chloroquinoline-3-carbaldehyde was obtained as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.95 (1 H, s), 9.19 (1 H, s), 8.33 (1 H, dd, J=8.5, 1.2 Hz), 8.20 (1 H, dd, J=7.3, 1.2 Hz), 7.95 (1 H, d, J=7.3 Hz), 7.74-7.87 (2 H, m), 7.63 (1 H, d, J=7.3 Hz) Mass Spectrum (ESI) m/e=336.1 and 338.0 (M+1)

Workup

  1. customPrepared
  2. customAfter purification

Sources & evidence

ORD record
ord-e7c7f23c0a4d4e71948e7a5179bdc036
Source dataset
uspto-grants-2011_04
Patent number
US07919498B2

Reaction notes

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