Dichloromethane → HCID 86723578, compound

HRID 918899Notes

Reaction equation

HRID 918899 reaction equation
[Br:1][C:2]1[C:3](=O)[NH:4][CH:5]=[C:6]([Br:8])[CH:7]=1.CO[C:12]1N=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.[CH2:21](Cl)Cl.[C:24]([O-:27])([O-])=O.[Cs+].[Cs+]>COCCOC>[CH2:3]([N:4]1[CH:5]=[C:6]([Br:8])[CH:7]=[C:2]([Br:1])[C:24]1=[O:27])[C:12]1[CH:21]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 6428263,5-Dibromo-2-hydroxypyridineHCID 2734368(6-Methoxypyridin-3-yl)boronic acid

Product 1

HCID 86723578HCID 86723578, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-bromo-5-methylisoxazol-3-amine (18, 0.35 g, 2 mmol), (6-methoxypyridin-3-yl)boronic acid (0.46 g, 1.5 equiv.), PdCl2dppf.CH2Cl2 (146 mg, 0.1 equiv) and Cs2CO3 (1.3 g, 2 equiv.) in aqueous DME (6 mL mixed with 0.5 mL H2O) was stirred at 100° C. for 5 h. The reaction mixture was allowed to cool to room temperature and filtered through a layer of Celite. The filtrate was concentrated and purified by chromatography (silica gel, 0-50% EtOAc in hexanes) to afford 19 (93 mg, 23%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.15 (dd, J=0.6, 2.4 Hz, 1H), 7.69 (dd, J=2.4, 8.7 Hz, 1H), 6.90 (dd, J=0.6, 8.4 Hz, 1H), 5.41 (s, 2H), 3.88 (s, 3H), 2.25 (s, 3H). ESI MS m/z 206 [M+H]+.

Workup

  1. filtrationfiltered through a layer of Celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by chromatography (silica gel, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-82740d6a9e7c4eaf9fe6d40b16524b96
Source dataset
uspto-grants-2016_03
Patent number
US09271978B2

Reaction notes

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