Methyl iodide → HCID 86679178, compound

HRID 1774827Notes

Reaction equation

HRID 1774827 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:13]=[C:14]([O:18][CH2:19][CH2:20][NH:21][S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[CH:15]=[N:16][CH:17]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:27].[H-].[Na+].[CH3:30]I>CN(C=O)C>[CH3:30][N:21]([CH2:20][CH2:19][O:18][C:14]1[CH:15]=[N:16][CH:17]=[C:12]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:2]([CH3:1])[C:3](=[O:27])[CH2:4][CH2:5]3)[CH:13]=1)[S:22]([CH2:25][CH3:26])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86679179HCID 86679179, compound

Product 1

HCID 86679178HCID 86679178, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethanesulfonic acid {2-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yloxy]-ethyl}-amide (example 151, 0.06 g, 0.154 mmol) in DMF (1.5 mL) cooled at 0° C. with an ice bath was added 60% NaH in mineral oil (0.008 g, 0.2 mmol) and the reaction mixture was stirred for 15 min. Then, MeI (0.026 g, 0.185 mmol) was added and the reaction mixture was stirred at 0° C. for another 30 min. The mixture was quenched with aq. ammonia (1 mL), diluted with brine (5 mL) and then extracted with EtOAc (2×20 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.050 g, 80%) as a light yellow amorphous solid. MS: 404.4 (M+H+).

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for another 30 min
  2. customThe mixture was quenched with aq. ammonia (1 mL)
  3. additiondiluted with brine (5 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. dry with materialCombined organics were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel flash chromatography
  9. washeluting with a 0 to 5% MeOH-DCM gradient

Sources & evidence

ORD record
ord-55157770ccef435d83dbbab2c38c0da7
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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