Methyl iodide → HCID 89995727, compound

HRID 523079Notes

Reaction equation

HRID 523079 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]([O:13]CC)=O.C[S-].[Na+].IC>C(O)C.O>[Br:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:9]=[CH:10][C:11](=[O:13])[NH:1]2)=[CH:4][N:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 4378561Sodium methanethiolateHCID 89995588Ethyl (E)-3-(4-Amino-6-bromo-3-pyridyl)acrylate

Product 1

HCID 89995727HCID 89995727, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(E)-Ethyl 3-(4-amino-6-bromopyridin-3-yl)acrylate (Preparation 68, 1.20 g 4.43 mmole) and sodium methanethiolate (320 mg 4.57 mmole) in ethanol (12 mL) were heated under microwave radiation at 80° C. for 25 minutes. Iodomethane (284 uL, 648 mg, 4.56 mmole) was added to the cooled reaction and the reaction was stirred at room temperature for 45 minutes before diluting with water (6 mL). The resulting precipitate was collected, washed with water and dried under high vacuum to afford the title compound (803 mg, 80%).

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-5ab58d83ac83468fafeea5ee6373e9fb
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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