Sodium ethoxide → HCID 22615145, compound

HRID 1457834Notes

Reaction equation

HRID 1457834 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].F[C:7]1[C:8]([CH:14]([N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:22])[CH3:15])=[N:9][CH:10]=[CH:11][C:12]=1[I:13]>C(O)C.O>[I:13][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([CH:14]([N:16]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:17]2[CH3:22])[CH3:15])[C:7]=1[O:1][CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 22615147HCID 22615147, compound

Product 1

HCID 22615145HCID 22615145, compoundYield 8.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium ethoxide was initially prepared by dissolving 2.0 g (87 mmole) of sodium metal in 300 ml of anhydrous absolute ethanol. To the stirring solution thus prepared was added 3.5 g (10.2 mmole) of N-[(3-Fluoro-4-iodopyrid-2-yl)eth-2-yl]-2,5-dimethylpyrrole and the mixture was refluxed under nitrogen for 4 days. The solution was cooled, diluted to 1 liter with water, and extracted with ethyl acetate (2×). The organic layer was dried over sodium sulfate, filtered, and concentrated to a resin. Chromatography over flash silica gel (30% ethyl acetate in hexanes) gave initially 320 mg (8.5%) of N-[(4-Iodo-3-ethoxypyrid-2-yl)-eth-2-yl]-2,5-dimethylpyrrole: 1H NMR (300 MHz, DMSO-d6) δ 7.95 (d, 1H), 7.62 (d, 1H), 5.80 (s, 2H), 4.10 (t, 2H), 4.00 (q, 2H), 3.15 (t, 2H), 2.20 (s, 6H), 1.45 (t, 3H); MS (FD) m/e 370 (Mt). Further elution provided the titled compound, 1.7 g (64%): IR (KBr, cm-1) 2991, 1608, 1495, 1309, 1075; 1H NMR (300 MHz, DMSO-d6) δ 8.22 (d, 1H), 7.15 (t, 1H), 5.60 (s, 2H), 4.20 (q, 2H), 4.10 (t, 2H), 2.98 (dt, 2H), 2.10 (s, 6H), 1.38 (t, 3H): MS (FD) m/e 262 (Mt). Anal. Calc'd. for C15H19FN2O 0.25 H2 O: C, 67.55; H, 7.31; N, 10.50. Found: C, 67.56; H, 7.35; N, 10.46.

Workup

  1. customTo the stirring solution thus prepared
  2. temperaturethe mixture was refluxed under nitrogen for 4 days
  3. temperatureThe solution was cooled
  4. extractionextracted with ethyl acetate (2×)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a resin

Sources & evidence

ORD record
ord-4c58f078efec42e3b4d99cf940eb480c
Source dataset
uspto-grants-1998_12
Patent number
US05849769

Reaction notes

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