Sodium Carbonate → HCID 24993714, compound

HRID 423589Notes

Reaction equation

HRID 423589 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]([C:21]([O:23][CH3:24])=[O:22])[C:18]([O:25][CH2:26][CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]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>[CH3:38][CH:36]([O:35][C:33]([N:30]1[CH2:31][CH2:32][CH:27]([CH2:26][O:25][C:18]2[C:19]([C:21]([O:23][CH3:24])=[O:22])=[N:20][C:15]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:16][CH:17]=2)[CH2:28][CH2:29]1)=[O:34])[CH3:37]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 86638742HCID 86638742, compound

Product 1

HCID 24993714HCID 24993714, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound (0.785 g, 82%) was prepared as a light yellow solid from [4-(methylsulfonyl)phenyl]boronic acid (0.48 g, 2.36 mmol), methyl 6-bromo-3-{[(1-{[(1-methylethyl)oxy]carbonyl}-4-piperidinyl)methyl]oxy}-2-pyridinecarboxylate (0.945 g, 86% pure), Pd(PPh3)2Cl2 (0.14 g, 0.20 mmol), 2M Na2CO3 (6 mL) and DME (20 mL) in a manner similar to Example 21, Step 3. The crude material was purified by chromatography on a silica gel column eluted with 1:10 acetone/CH2Cl2 followed by trituration with hot hexanes containing 1% of MeOH to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.15 (d, 2H, J=8.3 Hz), 8.01 (d, 2H, J=8.5 Hz), 7.86 (d, 1H, J=8.8 Hz), 7.41 (d, 1H, J=8.8 Hz), 4.92 (septet, 1H, J=6.2 Hz), 4.30-4.10 (m, 2H), 3.99 (s, 3H), 3.94 (d, 2H, J=6.3 Hz), 3.06 (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 491 (M+H).

Workup

  1. customThe crude material was purified by chromatography on a silica gel column
  2. washeluted with 1:10 acetone/CH2Cl2
  3. customto give the title compound

Sources & evidence

ORD record
ord-83fa3d259d7949508c44bf05532f6434
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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