Potassium Carbonate → (S)-tert-butyl 2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamate

HRID 874072Notes

Reaction equation

HRID 874072 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[N:11][CH:12]=1.Br[CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([O:13][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 58537397(S)-5-(1-Methylpyrrolidin-2-yl)pyridin-3-ol

Product 1

HCID 58537431(S)-tert-butyl 2-(5-(1-methylpyrrolidin-2-yl)pyridin-3-yloxy)ethylcarbamateYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-5-(1-Methylpyrrolidin-2-yl)pyridin-3-ol (preparation 10) (175 mg, 0.98 mmol), tert-butyl 2-bromoethylcarbamate (550 mg, 2.45 mmol) and potassium carbonate (676 mg, 4.9 mmol) in DMF (7 mL) were heated at 90° C. for 16 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate, dried over MgSO4 and evaporated. The crude product was purified by flash chromatography (5%→10% MeOH in DCM) to give the title compound as a yellow oil (108 mg, 34%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product was purified by flash chromatography (5%→10% MeOH in DCM)

Sources & evidence

ORD record
ord-f9183f1101484b18b550a9c7b67434f9
Source dataset
uspto-grants-2015_03
Patent number
US08980276B2

Reaction notes

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