HCID 18416192, compound → HCID 135690270, compound

HRID 990943Notes

Reaction equation

HRID 990943 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[N:8]=[C:7]([O:14][CH:15]([CH3:17])[CH3:16])[CH:6]=[C:5]2[C:18]([F:21])([F:20])[F:19]>CCOC(C)=O>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([O:14][CH:15]([CH3:17])[CH3:16])[CH:6]=[C:5]2[C:18]([F:21])([F:19])[F:20]

Participants

3

Reactant 1

HCID 18416192HCID 18416192, compound

Product 1

HCID 135690270HCID 135690270, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (60% mineral oil dispersion, 180 mg, 4.6 mmol, rinsed with hexanes) in 3.5 mL DMF was added thiophenol (550 mg, 5.0 mmol) at 0° C., whereupon a solution of 6-amino-2-isopropyloxy-7-methoxy-4-(trifluoromethyl)quinoline (200 mg, 0.67 mmol) in 2 mL DMF was added. The mixture was heated at 110° C. for 6 h, then poured into ice, and the pH was adjusted to 5 by the addition of 2N NaHSO4. The mixture was extracted with EtOAc (2×30 mL), washed sequentially with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered, and concentrated. Flash chromatography (4:1 hexanes:EtOAc) afforded 147 mg (77%) of 6-amino-2-isopropyloxy-7-methoxy-4-(trifluoromethyl)quinoline, a tan solid. Data for 6-amino-2-isopropyloxy-7-methoxy-4-(trifluoromethyl)quinoline: Rf 0.14 (4:1 hexanes:EtOAc); 1H NMR (500 MHz, CDCl3) δ 7.19 (broad s, 1H), 7.16 (s, 1H), 6.99 (s, 1H), 5.60 (v. broad s, 1H), 5.45 (hept, 1H, J=6.2), 4.00 (v. broad s, 2H), 1.38 (d, 6H, J=6.3).

Sources & evidence

ORD record
ord-f9fccd8973ac4ec8812f42ed13488c16
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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