Methyl iodide → HCID 14732816, compound

HRID 575851Notes

Reaction equation

HRID 575851 reaction equation
[C:1]1(=[O:10])[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[CH:3][NH:2]1.[H-].[Na+].[CH3:13]I>CN(C=O)C>[CH3:13][N:2]1[CH:3]=[CH:4][C:5]2[CH2:9][CH2:8][CH2:7][C:6]=2[C:1]1=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 147328152,5,6,7-Tetrahydro-1H-cyclopenta[c]pyridin-1-one

Product 1

HCID 14732816HCID 14732816, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The title compound of step 5 (260 mg, 1.93 mmol) was dissolved in DMF (5 mL) and cooled to 0° C. NaH (94 mg, 2.31 mmol) was added and the mixture was stirred for 30 min. Methyl iodide (146 μL, 2.31 mmol) was added and the mixture stirred at rt for 2 h. The volatile components were removed under vacuum and silica gel chromatography (PE/EtOAc=1:1) gave the title compound (192.6 mg, 67%) as a brown oil. 1H NMR (CD3Cl, 300 MHz): δ 7.13 (d, J=6.6 Hz, 1H), 6.13 (d, J=6.6 Hz, 1H), 3.53 (s, 3H), 2.79-2.85 (m, 4H), 2.01-2.11 (m, 2H).

Workup

  1. stirringthe mixture stirred at rt for 2 h
  2. customThe volatile components were removed under vacuum and silica gel chromatography (PE/EtOAc=1:1)

Sources & evidence

ORD record
ord-e7f450bfba26452db03edc93f70abdf0
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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