Dimethylformamide → HCID 10131118, compound

HRID 2216795Notes

Reaction equation

HRID 2216795 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:19][N:20](C)C=O>[C-]#N.[Zn+2].[C-]#N.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>[C:19]([C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1)#[N:20]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 9817826HCID 9817826, compound

Product 1

HCID 10131118HCID 10131118, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[3-bromophenyl]-4-[pyridin-2-yl]-1,3-oxazole (23 mg, 0.076 mmol) and zinc cyanide (112 mg, 0.96 mmol) in N,N-dimethylformamide (2 mL) was treated with Pd(PPh3)4 (74 mg, 0.064 mmol) and heated overnight at 80° C. Standard work up and chromatography afforded 6 mg (32%) of 2-[3-cyanophenyl]-4-[pyridin-2-yl]-1,3-oxazole as a white solid. 1H-NMR (CDCl3), δ (ppm): 8.61 (d, 1H), 8.45 (s, 1H), 8.38 (s, 1H), 8.36 (m, 1H), 8.00 (d, 1H), 7.80 (m, 2H), 7.61 (t, 1H), 7.23 (m, 1H).

Sources & evidence

ORD record
ord-74c8fff00ee249eb92b5d7a994b21e3e
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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