Methyl iodide → HCID 67168450, compound

HRID 1506469Notes

Reaction equation

HRID 1506469 reaction equation
I[CH3:2].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:9](=[C:14]([C:17]4[O:21][N:20]=[C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:18]=4[C:28]([F:31])([F:30])[F:29])[O:15][N:16]=3)[CH2:10][NH:11][C:12]=2[CH:13]=1.[H-].[Na+]>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]3[C:9](=[C:14]([C:17]4[O:21][N:20]=[C:19]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:18]=4[C:28]([F:31])([F:29])[F:30])[O:15][N:16]=3)[CH2:10][N:11]([CH3:2])[C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136350297HCID 136350297, compound

Product 1

HCID 67168450HCID 67168450, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodomethane (0.020 mL, 0.325 mmol) was slowly added to a stirred mixture of 7-bromo-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydroisoxazolo[4,3-c]quinoline (Preparation 77D, 0.050 g, 0.108 mmol) and sodium hydride (2.60 mg, 0.108 mmol) in THF (5.0 mL) at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with 1 N aqueous hydrochloric acid (10 mL) and extracted with ethyl acetate (3×25 mL). The ethyl acetate extract was dried over sodium sulfate and concentrated to give 7-bromo-5-methyl-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydroisoxazolo[4,3-c]quinoline (0.041 g, 0.084 mmol, 78%) as an orange solid. The product had an HPLC ret. time=4.45 min. (condition B). LC/MS M+1 478.0.

Workup

  1. customThe reaction mixture was quenched with 1 N aqueous hydrochloric acid (10 mL)
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. extractionThe ethyl acetate extract
  4. dry with materialwas dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a77bff5c26eb470683658ea3fcbff40d
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…