Sodium Carbonate → tert-Butyl 4-((2-chloro-5-phenylpyridin-4-ylamino)methyl)piperidine-1-carboxylate

HRID 556858

Reaction equation

HRID 556858 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[C:5](I)=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(#N)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[C:5]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59613389Tert-butyl 4-(((2-chloro-5-iodopyridin-4-yl)amino)methyl)piperidine-1-carboxylate

Product 1

HCID 59613323tert-Butyl 4-((2-chloro-5-phenylpyridin-4-ylamino)methyl)piperidine-1-carboxylateYield 99.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 4-((2-chloro-5-iodopyridin-4-ylamino)methyl)piperidine-1-carboxylate (0.100 g, 0.22 mmol), sodium carbonate (0.5 M, 0.66 mL), phenyl boronic acid (0.027 g, 0.221 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.011 g, 0.01 mmol) in acetonitrile (2 mL) was heated at 100° C. for 20 min under microwave irradiation. The reaction mixture was concentrated in vacuo. The crude product was purified by chromatography on a short silica column, eluting with ethyl acetate/petroleum ether (3/7), to give the title compound as a colourless oil (0.088 g, 98%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customThe crude product was purified by chromatography on a short silica column
  3. washeluting with ethyl acetate/petroleum ether (3/7)

Sources & evidence

ORD record
ord-6bcac72870cf437aa04cf86bab9e3388
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Linked notes

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