Sodium hydride → Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate

HRID 2269683Notes

Reaction equation

[N:1]([CH2:4][CH2:5][CH2:6][OH:7])=[N+:2]=[N-:3].[H-].[Na+].[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19](Br)[CH:18]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:16]=1)=[O:14])[CH3:11]>CN(C=O)C>[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19]([O:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[CH:18]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:16]=1)=[O:14])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Azido-1-propanol (0.266 mL, 3.64 mmol) was dissolved in DMF (5 mL) and cooled to 0° C. NaH (146 mg, 3.64 mmol) was added and the mixture was stirred for 15 minutes. Diethyl-4-bromo-2,6-pyridinedicarboxylate was dissolved in DMF (5 mL) an added to the reaction mixture dropwise. The reaction was complete as indicated by TLC in 1 hour. The reaction mixture was partitioned between CH2Cl2 and water. The water was separated and extracted with CH2Cl2. The CH2Cl2 layers were combined, dried (MgSO4) and concentrated to an oil. The oil was purified by silica gel flash column chromatography to give a yield of 40% 1H NMR (CDCl3) δ1.44 (t, 6H, 2x CH2), 2.11 (m, 2H, CH2), 3.54 (t, 2H, CH2), 4.23 (t, 2H, CH2), 4.45 (q, 4H, 2x CH2), 7.78 (2,H, 2x Ar)

Workup

additionan added to the reaction mixture dropwise
waitas indicated by TLC in 1 hour
customThe reaction mixture was partitioned between CH2Cl2 and water
customThe water was separated
extractionextracted with CH2Cl2
dry with materialdried (MgSO4)
concentrationconcentrated to an oil
customThe oil was purified by silica gel flash column chromatography
customto give a yield of 40% 1H NMR (CDCl3) δ1.44 (t, 6H, 2x CH2), 2.11 (m, 2H, CH2), 3.54 (t, 2H, CH2), 4.23 (t, 2H, CH2), 4.45 (q, 4H, 2x CH2), 7.78 (2,H, 2x Ar)

Sources & evidence

ORD record: ord-73dc36159773438186583ab3cbe5e7de
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329523B1

Reaction notes

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