Diisopropylethylamine → 6-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinonitrile

HRID 336262Notes

Reaction equation

HRID 336262 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.CCN(C(C)C)C(C)C.[C:18]([C:20]1[CH:21]=[C:22]([CH3:27])[C:23](F)=[N:24][CH:25]=1)#[N:19]>C(O)CCC.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:23]1[C:22]([CH3:27])=[CH:21][C:20]([C:18]#[N:19])=[CH:25][N:24]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1439532-(Methoxymethyl)pyrrolidineHCID 232882695-Cyano-2-fluoro-3-picoline

Product 1

HCID 675302276-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinonitrileYield 87%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

2-(Methoxymethyl)pyrrolidine (Acb-blocks C5A-0029; 406 mg; 3.53 mmol; 1.2 eq.) and DIEA (1.52 ml; 8.82 mmol; 3 eq.) were added to a solution of 5-cyano-2-fluoro-3-methylpyridine (400 mg; 2.94 mmol; 1 eq.) in 1-butanol (1 mL) and the reaction mixture was stirred at 90° C. for 16 hours. The reaction mixture was allowed to return to room temperature then diluted with ethyl acetate, washed with water, dried over magnesium sulphate and concentrated in vacuo to afford the title compound (0.59 g, 87%) as a yellow oil.

Workup

  1. customto return to room temperature
  2. washwashed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e86d9e4cc7d94d2387b0284e66532ff1
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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