Sodium Carbonate → 1-Methylethyl 4-[({2-fluoro-6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423583Notes

Reaction equation

HRID 423583 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:15]1[N:20]=[C:19]([F:21])[C:18]([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:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>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.COCCOC>[F:21][C:19]1[C:18]([O:22][CH2:23][CH:24]2[CH2:25][CH2:26][N:27]([C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31])[CH2:28][CH2:29]2)=[CH:17][CH:16]=[C:15]([C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)[N:20]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 866387411-Methylethyl 4-{[(6-bromo-2-fluoro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate

Product 1

HCID 591777431-Methylethyl 4-[({2-fluoro-6-[4-(methylsulfonyl)phenyl]-3-pyridinyl}oxy)methyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (197 mg, 70%) was prepared as a light gray solid from [4-(methylsulfonyl)phenyl]boronic acid (160 mg, 0.75 mmol), 1-methylethyl 4-{[(6-bromo-2-fluoro-3-pyridinyl)oxy]methyl}-1-piperidinecarboxylate (235 mg, 0.63 mmol), Pd(PPh3)2Cl2 (45 mg, 0.06 mmol), 2M Na2CO3 (4 mL) and DME (4 mL) in a manner similar to Example 21, Step 3. The crude product was triturated with MeOH to give the title compound as a light gray solid. 1H NMR (400 MHz, CDCl3): δ 8.12 (d, 2H, J=8.3 Hz), 7.99 (d, 2H, J=8.6 Hz), 7.63 (d, 1H, J=8.3 Hz), 7.40-7.30 (m, 1H), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.15 (m, 2H), 3.92 (d, 2H, J=6.4 Hz), 3.07 (s, 3H), 2.85-2.70 (m, 2H), 2.15-2.00 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (ESI), m/z 451 (M+H).

Workup

  1. customThe crude product was triturated with MeOH

Sources & evidence

ORD record
ord-d041856bcfd74b82a38e45ee31cbe9ad
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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