Isopropyl iodide → HCID 18416192, compound

HRID 990942Notes

Reaction equation

HRID 990942 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[CH:6]=[C:5]2[C:15]([F:18])([F:17])[F:16].[F-].[Cs+].[CH:21](I)([CH3:23])[CH3:22]>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([O:14][CH:21]([CH3:23])[CH3:22])[CH:6]=[C:5]2[C:15]([F:18])([F:16])[F:17]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 25953Cesium fluorideHCID 2794444HCID 2794444, compound

Product 1

HCID 18416192HCID 18416192, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to General Method 12 (EXAMPLE 22) from 6-amino-7-methoxy-4-(trifluoromethyl)-1H-quinolin-2-one (500 mg, 1.9 mmol), CsF (1.18 g, 7.7 mmol), isopropyl iodide (1.31 g, 7.7 mmol) in 8 mL DMF to afford 308 mg (53%) of 6-amino-2-isopropyloxy-7-methoxy-4-(trifluoromethyl)quinoline, a light yellow oil, and 190 mg (29%) of 2-isopropyloxy-7-methoxy-6N-(isopropyl)amino-4-(trifluoromethyl)quinoline, after flash chromatography (7:3 hexanes:EtOAc). Data for 6-amino-2-isopropyloxy-7-methoxy-4-(trifluoromethyl)quinoline: Rf 0.51 (4:1 hexanes:EtOAc); 1H NMR (500 MHz, CDCl3) δ 7.18 (s, 1H), 7.13 (broad s, 1H), 7.00 (s, 1H), 5.48 (hept, 1H, J=6.3), 4.11 (broad s, 2H), 4.01 (s, 3H), 1.40 (d, 6H, J=6.3).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-0a3eee441014406da2bbcedd6f5c49e6
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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