Sodium Carbonate → HCID 66672679, compound

HRID 423529Notes

Reaction equation

HRID 423529 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1.Br[C:16]1[N:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:16]2[N:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]3)=[CH:18][CH:17]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66672606(4-((2-Methoxyethyl)thio)phenyl)boronic acidHCID 866387374-(6-Bromopyridin-3-yloxymethyl)piperidine-1-carboxylic acid isopropyl ester

Product 1

HCID 66672679HCID 66672679, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-Methylethyl 4-({[6-(4-{[2-(methoxy)ethyl]thio}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate (0.19 g, 61%) was prepared as a light yellow solid from (4-{[2-(methoxy)ethyl]thio}phenyl)boronic acid (0.23 g, 75% pure, 0.80 mmol), 1-methylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (from Step 1, 0.25 g, 0.70 mmol), 2M Na2CO3 (2 mL) and PdCl2(PPh3)2 (50 mg, 0.07 mmol) in DME (3 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.34 (d, 1H, J=2.7 Hz), 7.86 (d, 2H, J=8.3 Hz), 7.64 (d, 1H, J=8.7 Hz), 7.42 (d, 2H, J=8.3 Hz), 7.30-7.25 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.23 (bs, 2H), 3.89 (d, 2H, J=6.3 Hz), 3.59 (t, 2H, J=6.7 Hz), 3.37 (s, 3H), 3.15 (t, 2H, J=6.8 Hz), 2.95-2.80 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 445 (M+H).

Sources & evidence

ORD record
ord-b80d8f4e6db6427d867fb5a4116578cc
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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