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Benzyl Alcohol → Benzyl 5-bromopyridin-3-ylcarbamate

HRID 1269178
Notes
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Reaction equation

HRID 1269178 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:18])C=CC=CC=1.CC[N:30]([CH2:33]C)CC.[CH2:35]([OH:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[C:6]([NH:30][C:33](=[O:18])[O:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:5]=[N:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 887075-Bromonicotinic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 18446849Benzyl 5-bromopyridin-3-ylcarbamateYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

To a suspension of 5-bromonicotinic acid (20.0 g, 99.0 mmol) in toluene (200 mL) was added diphenylphosphoryl azide (25.6 mL, 118.8 mmol) and Et3N (16.6 mL, 118.8 mmol). After stirring at room temperature for 30 min, benzyl alcohol (15.4 mL, 148.5 mmol) was added. The mixture was stirred at room temperature for 1 h then refluxed overnight. The cold reaction mixture was washed with H2O, NaHCO3 and brine, dried over MgSO4 and concentrated. Purification by flash chromatography (15–50% EtOAc/Hexane) provided 22.2 g (72.5 mmol, 73%) of benzyl 5-bromo-3-pyridinylcarbamate: ESMS m/e: 307.0 (M+H)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. temperaturethen refluxed overnight
  3. customThe cold reaction mixture
  4. washwas washed with H2O, NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (15–50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-51549b7691c444e3962cb407cfa05dde
Source dataset
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07199135B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes