Potassium Phosphate, Tribasic → 6-(2,3-Dimethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 25819

Reaction equation

HRID 25819 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:13])([CH3:12])[CH:6]=[C:5]2[CH3:14].[CH3:15][O:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:15][O:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:13])([CH3:12])[CH:6]=[C:5]2[CH3:14]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 51564912,3-Dimethoxybenzeneboronic acidHCID 107294646-Bromo-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 225665176-(2,3-Dimethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 61%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

6-Bromo-2,2,4-trimethyl-1,2-dihydroquinoline (256 mg, 1.02 mmol) (Example 8) and 2,3-dimethoxyphenyl boronic acid (370 mg, 2.03 mmol) were combined in DMSO (2 mL). 2 M K3PO4 (1 mL) was added, followed by PdCl2(dppf) (50 mg). The contents were placed in a microwave reaction vessel assembly and irradiated at 120° C. for 15 minutes. The reaction was cooled to room temperature. Purification of the crude product by chromatography afforded 6-(2,3-dimethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (190 mg, 61%) as a white solid.

Workup

  1. customThe contents were placed in a microwave reaction vessel assembly
  2. customirradiated at 120° C. for 15 minutes
  3. customPurification of the crude product by chromatography

Sources & evidence

ORD record
ord-7b25775c45f94861956773193f671d73
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Linked notes

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