Ethyl bromoacetate → 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-one

HRID 990932Notes

Reaction equation

HRID 990932 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]([OH:25])=[C:10]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:11]=2)[N:6]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34](OCC)=[O:35]>CN(C=O)C>[CH:1]([O:4][C:5]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[C:12]2[CH:11]=[C:10]3[N:19]([CH2:20][C:21]([F:22])([F:23])[F:24])[C:34](=[O:35])[CH2:33][O:25][C:9]3=[CH:8][C:7]=2[N:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 135690267HCID 135690267, compound

Product 1

HCID 184161447-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared by General Method 13 from 2-isopropyloxy-7-hydroxy-6-[(2,2,2-trifluoroethyl)amino]-4-(trifluoromethyl)quinoline (1.51 g, 4.10 mmol), K2CO3 (1.16 g, 8.40 mmol) and ethyl bromoacetate (0.719 g, 4.30 mmol) in 16.4 mL DMF to afford 1.57 g (94%) of 7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinolin-2(3H)-one, a light yellow-brown solid, Rf 0.50 (4:1 hexanes:EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.57 (broad s, 1H), 7.48 (s, 1H), 7.11 (s, 1H), 5.53 (hept, 1H, J=6.2), 4.79 (s, 2H), 4.71 (q, 2H, J=8.4), 1.41 (d, 6H).

Sources & evidence

ORD record
ord-28f3ef2a723543b0a8804ca98fe1f9c0
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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