Cesium carbonate → HCID 90410934, compound

HRID 626553Notes

Reaction equation

HRID 626553 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[C:58]([NH2:63])(=[O:62])[CH:59]([CH3:61])[CH3:60]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:63][C:58](=[O:62])[CH:59]([CH3:61])[CH3:60])[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 68424IsobutyramideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

Product 1

HCID 90410934HCID 90410934, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of Example A1 (2.00 g, 7.95 mmol), Cs2CO3 (5.00 g, 15.35 mmol), X-Phos (0.200 g, 0.420 mmol), Pd2(dba)3 (0.200 g, 0.218 mmol) and isobutyramide (1.00 g, 11.48 mmol) in dioxane (20 mL), under Ar, was heated at 90° C. overnight. The mixture was cooled to RT, the solids removed via filtration, washed with DCM and THF and the filtrate concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)isobutyramide (1.08 g, 45%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.65 (s, 1H), 8.58 (m, 1H), 8.41 (dd, J=8.9, 0.5 Hz, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.99 (dd, J=8.9, 2.8 Hz, 1H), 7.85 (d, J=2.4 Hz, 1H), 6.89 (dd, J=5.7, 2.4 Hz, 1H), 2.72 (m, 1H), 1.03 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 303.1 (M+H+).

Workup

  1. customthe solids removed via filtration
  2. washwashed with DCM and THF
  3. concentrationthe filtrate concentrated to dryness
  4. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-50f996831eba482d9095d63ece1834d1
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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