Sodium Carbonate → N-(3-(2-Methoxybenzyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

HRID 392446Notes

Reaction equation

HRID 392446 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 23521695N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine

Product 1

HCID 23521678N-(3-(2-Methoxybenzyl)phenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

The flask was charged with N-(3-bromomethylphenyl)-N-(ethylsulfonyl)pyrid-3-ylmethylamine (0.180 g, 0.500 mmol), 2-methoxyphenylboronic acid (0.113 g, 0.75 mmol), 4.5 ml of DME, 1.5 ml of 2 M Na2CO3, and terakis(triphenylphosphine) palladium(0) (0.018 g, 0.016 mmol). After N2-flushing, the mixture was heated at 50° C. overnight. The reaction mixture was concentrated, diluted with water, and extracted with EtOAc. The organic layer was washed with brine and concentrated. The residue was chromatographed on a silica-gel column with 1:1 to 1:3 toluene/EtOAc to afford the title compound. 1H NMR:, 8.37 (d,1H,J=3.9 Hz), 8.24 (s,1H), 7.55 (d,1H,J=7.8 Hz), 6.74-7.17 (m,9H), 4.76 (s,2H), 3.80 (s,2H), 3.69 (s,2H), 2.94 (q,2H,J=7.3 Hz), 1.32 (t,3H,J=7.3 Hz). MS calcd. 396.2; MS (M+1) 397.2.

Workup

  1. customAfter N2-flushing
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica-gel column with 1:1 to 1:3 toluene/EtOAc

Sources & evidence

ORD record
ord-3eff67a610a14024858f68e130218ea1
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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