Methyl iodide → 7-Bromo-2-methyl-1,6-naphthyridine

HRID 523077Notes

Reaction equation

HRID 523077 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)[CH3:12].C[S-].[Na+].IC>C(O)C>[Br:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:9]=[CH:10][C:11]([CH3:12])=[N:1]2)=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 4378561Sodium methanethiolateHCID 89995621(E)-4-(4-Amino-6-bromopyridin-3-yl)but-3-en-2-one

Product 1

HCID 899956197-Bromo-2-methyl-1,6-naphthyridineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-4-(4-Amino-6-bromopyridin-3-yl)but-3-en-2-one (Preparation 66, 331 mg 1.37 mmol) and sodium thiomethoxide (97.5 mg 1.39 mmol) were stirred in ethanol (2.9 mL) at 20° C. for 50 minutes. Iodomethane (86 uL, 1.38 mmole) was added and the reaction stirred for another 45 minutes. The reaction was concentrated in vacuo and diluted with ethyl acetate (30 mL) and washed with water (10 mL). The aqueous was back extracted with ethyl acetate (5 mL) and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound (275 mg, 89%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with ethyl acetate (30 mL)
  3. washwashed with water (10 mL)
  4. extractionThe aqueous was back extracted with ethyl acetate (5 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77f27829e73446deb99cc615115187ac
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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