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Potassium Carbonate → Tert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylate

HRID 2036137
Notes
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Reaction equation

HRID 2036137 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.CS(O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=O)=O.C1OCCOCCOCCOCCOCCOC1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[Br:1][C:2]1[N:3]=[CH:4][C:5]([O:8][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178516739HCID 178516739, compound

Product 1

HCID 58456669Tert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Procedure

A mixture of 5-bromopyrazin-2-ol B4a (525 mg, 3 mmol), tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (1.117 g, 4 mmol), 18-crown-6 (79 mg, 0.3 mmol), K2CO3 (829 mg, 6 mmol) in butan-2-one (19 mL) is subjected to microwave irradiation at 130° C. for 15 min. The solids are filtered off, washed with ethyl acetate and purified by flash chromatography (hexanes/ethyl acetate gradient) to afford tert-butyl 4-(5-bromopyrazin-2-yloxy)piperidine-1-carboxylate B4b as a white solid: MS calcd. For C14H21BrN3O3 ([M+H]+): 358.1, found: 358.1.

Workup

  1. customirradiation at 130° C. for 15 min
  2. filtrationThe solids are filtered off
  3. washwashed with ethyl acetate
  4. custompurified by flash chromatography (hexanes/ethyl acetate gradient)

Sources & evidence

ORD record
ord-142c23ec296f4fcdb8bcad1863ec1dec
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575168B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes