Methyl iodide → HCID 18416133, compound

HRID 990935Notes

Reaction equation

HRID 990935 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:16][O:15][C:14]2[C:5](=[CH:6][C:7]3[C:8]([C:21]([F:24])([F:23])[F:22])=[CH:9][C:10]([O:17][CH:18]([CH3:20])[CH3:19])=[N:11][C:12]=3[CH:13]=2)[N:4]1[CH2:25][C:26]([F:29])([F:28])[F:27].[H-].[Na+].I[CH3:33]>C1COCC1>[CH:18]([O:17][C:10]1[CH:9]=[C:8]([C:21]([F:22])([F:23])[F:24])[C:7]2[CH:6]=[C:5]3[N:4]([CH2:25][C:26]([F:28])([F:29])[F:27])[CH:3]([CH2:2][O:1][CH3:33])[CH2:16][O:15][C:14]3=[CH:13][C:12]=2[N:11]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18416140HCID 18416140, compound

Product 1

HCID 18416133HCID 18416133, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared by General Method 16 from (±)-2,3-dihydro-2-(hydroxymethyl)-7-isopropoxy-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline (EXAMPLE 28) (10 mg, 0.024 mmol), NaH (4.7 mg, 0.12 mmol) and iodomethane (17 mg, 0.12 mmol) in 0.6 mL THF to afford 8.3 mg (81%) of (±)-2,3-dihydro-7-isopropoxy-2-(methoxymethyl)-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline, a yellow solid, after flash chromatography (5:1 hexanes:EtOAc). Data for (±)-2,3-dihydro-7-isopropoxy-2-(methoxymethyl)-1-(2,2,2-trifluoroethyl)-9-(trifluoromethyl)-1H-[1,4]oxazino[3,2-g]quinoline: Rf 0.21 (3:1 hexanes: EtOAc); 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1H), 7.14 (broad s, 1H), 7.00 (s, 1H), 5.48 (hept, 1H, J =6.2), 4.43 (dd, 1H, J=11.0, 1.6), 4.16 (dd, J=11.0, 2.6), 3.98-4.21 (m, 2H), 3.67-3.73 (m, 1H), 3.50-3.60 (m, 2H), 3.37 (s, 3H), 1.38 (d, 6H, J=6.2).

Sources & evidence

ORD record
ord-041b42fa48724ab084c448c1b4ba4e0b
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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