Allyl bromide → methyl 3-(allyl(tetrahydro-2H-pyran-4-yl)amino)-5-chloro-2-methylbenzoate

HRID 2208898Notes

Reaction equation

HRID 2208898 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].Br[CH2:23][CH:24]=[CH2:25]>CN(C=O)C>[CH2:25]([N:13]([CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[C:4]1[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([Cl:1])[CH:3]=1)[C:7]([O:9][CH3:10])=[O:8])[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 70873657HCID 70873657, compound

Product 1

HCID 86719567methyl 3-(allyl(tetrahydro-2H-pyran-4-yl)amino)-5-chloro-2-methylbenzoateYield 46.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 5-chloro-2-methyl-3-((tetrahydro-2H-pyran-4-yl)amino)benzoate (1.0 g, 3.3 mmol) in DMF (10 mL), NaH (0.25 g, 10 mmol) was added at 0° C. and the mixture stirred for 20 minutes. 3-bromoprop-1-ene (1.7 g, 14.13 mmol) was added and the mixture was heated at 80° C. for 15 h. On completion, the reaction was quenched with ice cold water and extraction was carried out using DCM. The combined organic layers were dried, concentrated and resulting crude was purified by column chromatography giving the title compound (0.50 g, 44%).

Workup

  1. customOn completion, the reaction was quenched with ice cold water and extraction
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customresulting crude
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9716e70efb1c40b79bf5922f5d633b47
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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