Methyl N-(triethylammoniosulfonyl)carbamate → 2-Bromo-6-[(5-cyclopropyl-1,3,4-oxadiazol-2-yl)methyl]pyridine

HRID 386081Notes

Reaction equation

HRID 386081 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([NH:11][NH:12][C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])=O)[CH:5]=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH2:8][C:9]2[O:14][C:13]([CH:15]3[CH2:17][CH2:16]3)=[N:12][N:11]=2)[N:7]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59525662N'-[2-(6-bromopyridin-2-yl)acetyl]cyclopropanecarbohydrazide

Product 1

HCID 595261632-Bromo-6-[(5-cyclopropyl-1,3,4-oxadiazol-2-yl)methyl]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

N′-[2-(6-Bromopyridin-2-yl)acetyl]cyclopropanecarbohydrazide (200 mg, 0.67 mmol) and Burgess reagent (320 mg, 1.34 mmol) were combined in THF (4.0 mL) and heated at 100° C. for 25 min in a microwave. The reaction mixture was concentrated and directly purified by flash chromatography (10-100% EtOAc/hexanes) to afford the title compound as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customdirectly purified by flash chromatography (10-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-da746f927d5e450e9106f8e89c57154a
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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