Potassium Carbonate → HCID 86638742, compound

HRID 423588Notes

Reaction equation

HRID 423588 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1.CS(O[CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22175135Methyl 6-bromo-3-hydroxypicolinateHCID 57930057Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate

Product 1

HCID 86638742HCID 86638742, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 6-bromo-3-{[(1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinyl)methyl]oxy}-2-pyridinecarboxylate (0.945 g, 86% pure) was prepared as a colorless oil from methyl 6-bromo-3-hydroxy-2-pyridinecarboxylate (0.70 g, 2.78 mmol), 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 131, Step 4, 1.23 g, 4.16 mmol) and K2CO3 (0.78 g, 5.55 mmol) in DMF (30 mL) in a manner similar to Example 131, Step 5. The crude product was purified by flash chromatography on an ISCO silica gel column using 0 to 45% EtOAc/hexanes. 1H NMR (400 MHz, CDCl3): δ 7.53 (d, 1H, J=8.5 Hz), 7.21 (d, 1H, J=8.8 Hz), 4.91 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 2H), 3.93 (s, 3H), 3.86 (d, 2H, J=6.3 Hz), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.75 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 415/417 (M+H).

Workup

  1. customThe crude product was purified by flash chromatography on an ISCO silica gel column

Sources & evidence

ORD record
ord-53352efa82ca4c9ca97faa78823d9bbb
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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