Dimethylformamide → HCID 68671186, compound

HRID 2071158Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[C:11](Br)[CH:10]=[C:9]([CH3:14])[N:8]=1)=[O:4].[NH4+].[OH-].CCOC(C)=O.[CH3:25][N:26](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]([F:16])([F:15])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[C:11]([C:25]#[N:26])[CH:10]=[C:9]([CH3:14])[N:8]=1)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.93 g of (4-bromo-6-methylpyridin-2-yl)methyl 2,2,2-trifluoroacetate in 10 mL of DMF (degassed) was added 667 mg (5.68 mmol) of Zn(CN)2 and 689 mg (0.600 mmol) of Pd(PPh3)4. The mixture was stirred at 80° C. for about 4 h, and 233 mg of Pd(PPh3)4 was added. After 2.5 h, 50 mL of 10% NH4OH solution, and EtOAc were added. The aqueous layer was extracted with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1 to 5) % MeOH/CHCl3 provided 1.20 g of (4-cyano-6-methylpyridin-2-yl)methyl 2,2,2-trifluoroacetate as a yellow solid with some impurity.

Workup

waitAfter 2.5 h
extractionThe aqueous layer was extracted with EtOAc
washthe combined extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by flash silica gel chromatography (1 to 5) % MeOH/CHCl3

Sources & evidence

ORD record: ord-aa8f2fb2001d4d618f149708755ff402
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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