Thiophenol → HCID 135690269, compound

HRID 990944Notes

Reaction equation

HRID 990944 reaction equation
[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[C:7](=[CH:8][C:9]([O:23]C)=[C:10]([NH:19][CH:20]([CH3:22])[CH3:21])[CH:11]=2)[N:6]=1)([CH3:3])[CH3:2].C1(S)C=CC=CC=1.[H-].[Na+].OS([O-])(=O)=O.[Na+]>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[C:12]2[C:7](=[CH:8][C:9]([OH:23])=[C:10]([NH:19][CH:20]([CH3:22])[CH3:21])[CH:11]=2)[N:6]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 516919Sodium BisulfateHCID 18416132HCID 18416132, compound

Product 1

HCID 135690269HCID 135690269, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-isopropyloxy-6-isopropylamino-7-methoxy-4-(trifluoromethyl)quinoline (0.10 g, 0.30 mmol), thiophenol (0.24 g, 2.2 mmol), and NaH (60% dispersion in mineral oil, 78 mg, 2.0 mmol) in 2 mL DMF was heated at 110° C. for 5 h, whereupon the mixture was poured over ice, and adjusted to pH 5 with 2M NaHSO4. The aqueous layer was extracted with EtOAc (2×), and the combined organic layers were washed sequentially with water (2×) and brine, dried over MgSO4, filtered and concentrated. Flash chromatography (4:1 hexanes:EtOAc) afforded 90 mg (95%) of 2-isopropyloxy-7-hydroxy-6-isopropylamino-4-(trifluoromethyl)quinoline, a yellow oil. Data for 2-isopropyloxy-7-hydroxy-6-isopropylamino-4-(trifluoromethyl)quinoline: 1H NMR (400 MHz, CDCl3) δ 7.16 (s, 1H), 6.98 (s, 1H), 6.92 (s, 1H), 5.37 (sept, 1H, J=6.2), 3.70 (sept, 1H, J=6.3), 1.35 (d, 6H, J=6.2), 1.29 (d, 6H, J=6.3).

Workup

  1. additionwas poured over ice
  2. extractionThe aqueous layer was extracted with EtOAc (2×)
  3. washthe combined organic layers were washed sequentially with water (2×) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f474a6e1b43e40ba886a5510b83788fa
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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