Dimethylformamide → HCID 178464134, compound

HRID 1170428Notes

Reaction equation

HRID 1170428 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:34])[C:17]2[C:12](=[CH:13][C:14](I)=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33].C(=O)(O)[O-].[Na+].[CH3:40][N:41](C)C=O>[C-]#N.[Zn+2].[C-]#N>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:34])[C:17]2[C:12](=[CH:13][C:14]([C:40]#[N:41])=[CH:15][C:16]=2[C:18]([F:21])([F:20])[F:19])[N:11]([CH2:23][C@H:24]2[CH2:27][C@H:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH2:25]2)[C:10]1=[O:33]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 178464138HCID 178464138, compound

Product 1

HCID 178464134HCID 178464134, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

To a solution of the compound of Example 1-2 (68 mg, 0.11 mmol) in N,N-dimethylformamide (1.1 mL) were added zinc cyanide (15 mg, 0.13 mmol) and tetrakistriphenylphosphine palladium (25 mg, 0.02 mmol), and the reaction was carried out at 80° C. for 2 hours. To the reaction solution was added saturated aqueous sodium bicarbonate, and the mixture was extracted with toluene-ethyl acetate (1:1). The organic layer was dried over magnesium sulfate and filtered, and then evaporated and purified by silica gel column chromatography (chloroform/methanol/ammonia water=50/1/0 to 10/1/0 to 100/10/1) to give the titled compound (54 mg, 94%).

Workup

  1. extractionthe mixture was extracted with toluene-ethyl acetate (1:1)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. custompurified by silica gel column chromatography (chloroform/methanol/ammonia water=50/1/0 to 10/1/0 to 100/10/1)

Sources & evidence

ORD record
ord-3eb0827545c44e98952a89232e6c711d
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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