Cesium carbonate → HCID 86655135, compound

HRID 1045920Notes

Reaction equation

HRID 1045920 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][C:11]1[CH:22]=[CH:21][CH:20]=[CH:19][C:12]=1[C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH:10][C:11]2[CH:22]=[CH:21][CH:20]=[CH:19][C:12]=2[C:13]([N:15]([O:17][CH3:18])[CH3:16])=[O:14])[C:5]([Cl:9])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 110522422-amino-N-methoxy-N-methylbenzamideHCID 534009652,5-Dichloro-4-iodopyridine

Product 1

HCID 86655135HCID 86655135, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Palladium(II) acetate (0.066 g, 0.29 mmol) was added to 2,5-dichloro-4-iodopyridine (2 g, 7.30 mmol), 2-amino-N-methoxy-N-methylbenzamide (1.316 g, 7.30 mmol), cesium carbonate (4.76 g, 14.60 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.254 g, 0.44 mmol) in dioxane (100 mL) under an atmosphere of nitrogen. The resulting suspension was heated at 80° C. for 18 hours and then allowed to cool to room temperature. The mixture was filtered and the filtrate evaporated. The residue was purified by chromatography on silica, eluting with a gradient of 0-5% MeOH in CH2Cl2. Fractions containing product were combined and evaporated to afford 2-[(2,5-dichloropyridin-4-yl)amino]-N-methoxy-N-methylbenzamide (0.775 g, 33% yield); 1H NMR spectrum: (300 MHz, DMSO) δ 3.18 (3H, s), 3.48 (3H, s), 6.61 (1H, d), 7.34-7.40 (1H, m), 7.45-7.47 (1H, m), 7.54-7.57 (2H, m), 8.19 (1H, s), 8.47 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+=326.0 and 328.0 and 330.0.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated
  4. customThe residue was purified by chromatography on silica
  5. washeluting with a gradient of 0-5% MeOH in CH2Cl2
  6. additionFractions containing product
  7. customevaporated

Sources & evidence

ORD record
ord-7656fd7540a742b58ed423b641e741e0
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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