Sodium Carbonate → HCID 23521672, compound

HRID 392461Notes

Reaction equation

HRID 392461 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:10]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 23521674HCID 23521674, compound

Product 1

HCID 23521672HCID 23521672, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(1-(4-bromophenyl)ethyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (200 mg, 0.52 mmol), 2,4-difluorophenylboronic acid (124 mg, 0.78 mmol), sodium carbonate (0.78 ml of a 2M aqueous solution, 1.56 mmol), and tetrakis(triphenylphosphine)palladium(0) (26 mg, 0.023 mmol), under a nitrogen atmosphere was refluxed in dioxane (8 ml) for 6 h, then cooled to room temperature. The mixture was concentrated to a tan residue and resuspended in 2 ml dichloromethane. The suspension was subjected to purification by radial chromatography on a 2 micron silica plate eluting with 2 to 4% methanol/dichloromethane to afford the title compound. 1H NMR: 8.45 (bs,1H), 8.37 (bs,1H), 7.62 (d,1H,J=8 Hz), 7.45 (m,5H), 7.15 (m,1H), 6.95 (m,2H), 5.30 (q,1H,J=8 Hz), 4.35 (s,2H), 2.92 (q,2H,J=8 Hz), 1.67 (d,3H,J=8 Hz), 1.37 (t,3H,J=8 Hz). MS calcd. 416.5; MS (M+1) 417.1.

Workup

  1. concentrationThe mixture was concentrated to a tan residue
  2. customThe suspension was subjected to purification by radial chromatography on a 2 micron silica plate
  3. washeluting with 2 to 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-181b9eb5bee24ec0be8443c38414a51b
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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