Sodium Carbonate → 1-Methylethyl 4-[({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423585Notes

Reaction equation

HRID 423585 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:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[N:19][CH:20]=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>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[N:16]=[CH:17][C:18]([O:21][CH2:22][CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]3)=[N:19][CH:20]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 57930233HCID 57930233, compound2×

Product 1

HCID 249937131-Methylethyl 4-[({5-[4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)methyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (0.303 g, 61%) was prepared as a white solid from [4-(methylsulfonyl)phenyl]boronic acid (0.28 g, 1.37 mmol), 1-methylethyl 4-{[(5-bromo-2-pyrazinyl)oxy]methyl}-1-piperidinecarboxylate (crude material prepared in Step 2), Pd(PPh3)2Cl2 (82 mg, 0.11 mmol), 2M Na2CO3 (8 mL) and DME (8 mL) in a manner similar to Example 21, Step 3. The crude material was purified by flash chromatography on a silica gel column eluted with 1:20 acetone/CH2Cl2 to 1:10 acetone/CH2Cl2 followed by trituration with hot hexanes containing 1% MeOH to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.56 (s, 1H), 8.31 (s, 1H), 8.12 (d, 2H, J=8.3 Hz), 8.03 (d, 2H, J=8.3 Hz), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 4H), 3.09 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.90-1.80 (m, 2H), 1.40-1.20 (m, 8H); LRMS (ESI), m/z 434 (M+H).

Workup

  1. customThe crude material was purified by flash chromatography on a silica gel column
  2. washeluted with 1:20 acetone/CH2Cl2 to 1:10 acetone/CH2Cl2

Sources & evidence

ORD record
ord-a7ef1d8b8a4e45b5b1375e1ea04b42b8
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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