Sodium Carbonate → HCID 15085984, compound

HRID 1073285Notes

Reaction equation

HRID 1073285 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=2)[C:6]=1[NH2:23])=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1>O1CCCC1.C1(C)C=CC=CC=1.C(O)C.OO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([C:32]3[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=3)=[CH:18][CH:17]=2)[C:6]=1[NH2:23])=[O:4]

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 15085977HCID 15085977, compound

Product 1

HCID 15085984HCID 15085984, compound

Reagents, catalysts & solvents 5

HCID 784Hydrogen PeroxideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a degassed solution of 0.39 g of 3-amino-6-fluoro-2-(4-iodophenyl)-4-quinolinecarboxylic acid methyl ester and 0.035 g of tetrakis(triphenylphosphine) palladium in 10 ml of tetrahydrofuran and 10 ml toluene was added 1.0 ml of 2M aqueous sodium carbonate followed by a solution of 0.148 g of 3-pyridine boronic acid in 2 ml of ethanol. The mixture was stirred at reflux under argon for 5 hours and then cooled to 20° C. Two drops of 30% hydrogen peroxide were added and the mixture stirred for 30 minutes. The reaction mixture was partitioned between water and methylene chloride The organic layers were washed with water and dried over sodium sulfate. The volatiles were removed in vacuo, giving a tan powder. The crude product was purified via silica gel chromatography using toluene/acetone/methanol 78:20:2 as the eluent. The desired compound was obtained as yellow crystals (0.132g), mp 178°-183° C.

Workup

  1. temperatureat reflux under argon for 5 hours
  2. stirringthe mixture stirred for 30 minutes
  3. customThe reaction mixture was partitioned between water and methylene chloride The organic layers
  4. washwere washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe volatiles were removed in vacuo
  7. customgiving a tan powder
  8. customThe crude product was purified via silica gel chromatography

Sources & evidence

ORD record
ord-1dcad05834294c2dae4c451a240bbd3e
Source dataset
uspto-grants-1990_11
Patent number
US04968702

Reaction notes

Loading…