Methyl iodide → 7-(3,5-Dimethylisoxazol-4-yl)-1-methyl-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 589094Notes

Reaction equation

HRID 589094 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[CH:15][C:14]3[NH:17][C:18](=[O:19])[N:12]4[C:13]=3[C:8]=2[CH2:9][CH2:10][CH:11]4[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:5]([CH3:26])[O:4][N:3]=1.[C:27](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[CH:15][C:14]3[N:17]([CH3:27])[C:18](=[O:19])[N:12]4[C:13]=3[C:8]=2[CH2:9][CH2:10][CH:11]4[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:5]([CH3:26])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 904098527-(3,5-Dimethylisoxazol-4-yl)-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Product 1

HCID 904100527-(3,5-Dimethylisoxazol-4-yl)-1-methyl-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-oneYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(3,5-dimethylisoxazol-4-yl)-4-phenyl-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (10.7 g, 0.031 mmol) in N,N-dimethylformamide (0.50 mL) was treated with cesium carbonate (20.2 g, 0.062 mmol) followed by methyl iodide (2.9 μL, 46.5 μmol) and stirred at room temperature for 16 h. Purification via preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min) gave the desired product (8.2 mg, 74%) as a racemic mixture. 1H NMR (400 MHz, CDCl3) δ 7.35-7.20 (m, 3H), 7.03 (d, J=6.9 Hz, 2H), 6.99-6.93 (m, 1H), 6.93-6.84 (m, 1H), 5.53 (s, 1H), 3.49 (s, 3H), 2.48-2.11 (m, 7H), 2.09-1.84 (m, 3H); LCMS calculated for C22H22N3O2 (M+H)+: m/z=360.2. found: 360.1.

Workup

  1. customPurification via preparative LCMS (XBridge C18 column
  2. washeluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-b606733fc7ed4cb3958c8b6e99c4fe59
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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