Sodium Carbonate → 1,1-Dimethylethyl 4-({[6-(4-{[3-(methoxy)propyl]thio}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate

HRID 423536Notes

Reaction equation

HRID 423536 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][CH:8]=1.Br[C:17]1[N:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[CH:19][CH:18]=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][CH2:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([C:17]2[N:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]3[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29][CH2:30]3)=[CH:19][CH:18]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 579302011,1-Dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylateHCID 66673570(4-{[3-(Methoxy)propyl]thio}phenyl)boronic acid

Product 1

HCID 666731231,1-Dimethylethyl 4-({[6-(4-{[3-(methoxy)propyl]thio}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylateYield 86.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1,1-Dimethylethyl 4-({[6-(4-{[3-(methoxy)propyl]thio}phenyl)-3-pyridinyl]oxy}methyl)-1-piperidinecarboxylate (0.384 g, 86%) was prepared as a yellow solid from (4-{[3-(methoxy)propyl]thio}phenyl)boronic acid (0.27 g, 1.13 mmol), 1,1-dimethylethyl 4-{[(6-bromo-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 76, Step 1, 0.35 g, 0.94 mmol), 2M Na2CO3 (5 mL) and PdCl2(PPh3)2 (68 mg, 0.09 mmol) in DME (6 mL) in a manner similar to Example 21, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.34 (d, 1H, J=2.2 Hz), 7.84 (d, 2H, J=8.3 Hz), 7.63 (d, 1H, J=8.8 Hz), 7.39 (d, 2H, J=8.3 Hz), 7.25-7.20 (m, 1H), 4.17 (bs, 2H), 3.88 (d, 2H, J=6.3 Hz), 3.48 (t, 2H, J=6.0 Hz), 3.32 (s, 3H), 3.04 (t, 2H, J=7.2 Hz), 2.85-2.70 (m, 2H), 2.05-1.80 (m, 5H), 1.46 (s, 9H), 1.35-1.20 (m, 2H); LRMS (ESI), m/z 473 (M+H).

Sources & evidence

ORD record
ord-24ca0e6c548541ef84728f73c5b7c8ac
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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