Cesium fluoride → HCID 66762983, compound

HRID 2368170Notes

Reaction equation

HRID 2368170 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([Cl:29])[CH:23]=2)=[CH:6][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9].C([Sn](CCCC)(CCCC)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)CCC.[F-].[Cs+]>CN(C=O)C.[Cu]I.[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>[Cl:29][C:24]1[CH:23]=[C:22]([C:5]2[N:4]=[N:3][C:2]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[C:7]([C:8]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)=[O:9])[CH:6]=2)[CH:27]=[C:26]([CH3:28])[CH:25]=1

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 6077842-(Tributylstannyl)pyridineHCID 86662438HCID 86662438, compound

Product 1

HCID 66762983HCID 66762983, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-chloro-6-(3-chloro-5-methylphenyl)-N-(3,4-dimethoxybenzyl)pyridazine-4-carboxamide (3-1, 0.01 g, 0.023 mmol, 1.0 equiv; made analogously to 1-3) in DMF (0.50 mL) at 25° C. was added 2-tributylstannylpyridine (0.017 g, 0.046 mmol, 2.0 equiv), cesium fluoride (0.007 g, 0.046 mmol, 2.0 equiv), copper (I) iodide (0.00044 g, 0.0023 mmol, 0.1 equiv), and tetrakis(triphenylphosphine) palladium(0) (0.0027 g, 0.0023 mmol, 0.1 equiv) and the reaction mixture was heated to 80° C. for 0.5 hours. The reaction was cooled and partitioned between EtOAc and water. The organic phase was dried over MgSO4 and concentrated. The reaction mixture was purified by normal phase column chromatography (0 to 100% EtOAc in hexanes) to give the product (3-2) as a tan solid. HRMS [M+H] C25H27ClN4O4 calc'd 475.1531. found 475.1549.

Workup

  1. customat 25° C.
  2. temperatureThe reaction was cooled
  3. custompartitioned between EtOAc and water
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe reaction mixture was purified by normal phase column chromatography (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f466159ce4f54272bb43eb39d71fb7e4
Source dataset
uspto-grants-2014_04
Patent number
US08703770B2

Reaction notes

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