Iodoethane → Tert-butyl 5-bromopyridin-2-YL(ethyl)carbamate

HRID 881497Notes

Reaction equation

HRID 881497 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].I[CH2:19][CH3:20]>C1COCC1>[C:4]([O:3][C:1](=[O:2])[N:8]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1)[CH2:19][CH3:20])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 162178432-(Boc-amino)-5-bromopyridine

Product 1

HCID 53217453Tert-butyl 5-bromopyridin-2-YL(ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(BOC-amino)-5-bromopyridine (500 mg) in THF (20 mL) at 0° C. was added sodium hydride (88 mg) and the reaction stirred for 20 min. Then, iodoethane (0.18 mL) was added and the reaction stirred at room temperature for 16 h. The reaction was quenched with water (20 mL) and extracted into ethylacetate (3×20 mL). The organic layers were dried (MgSO4) and reduced in vacuo to give (5-bromo-pyridin-2-yl)-ethyl-carbamic acid tert-butyl ester as a white solid.

Workup

  1. stirringthe reaction stirred at room temperature for 16 h
  2. customThe reaction was quenched with water (20 mL)
  3. extractionextracted into ethylacetate (3×20 mL)
  4. dry with materialThe organic layers were dried (MgSO4)

Sources & evidence

ORD record
ord-be7e108d54264f218dee7d8c0e2592e1
Source dataset
uspto-grants-2015_03
Patent number
US08993563B2

Reaction notes

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