Dimethylformamide → HCID 69299447, compound

HRID 2196526Notes

Reaction equation

HRID 2196526 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][C:10]([C:18]([F:21])([F:20])[F:19])=[N:9]2)[N:3]=1.[CH3:22][N:23](C=O)C>[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>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:12]1[N:8]([C:4]2[N:3]=[C:2]([C:22]#[N:23])[CH:7]=[CH:6][CH:5]=2)[N:9]=[C:10]([C:18]([F:21])([F:20])[F:19])[CH:11]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86624647HCID 86624647, compound

Product 1

HCID 69299447HCID 69299447, compoundYield 11.9%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 45 (588 mg, 1.88 mmol) in DMF (12.5 mL) was added zinc cyanide (0.238 mL, 3.75 mmol) followed by Pd(PPh3)4 (217 mg, 0.187 mmol). The resulting suspension was allowed to stir at 95° C. overnight. The residue was purified via ISCO flash chromatography (5% to 35% EtOAc/Hexane; 40G column). The title product 46 (68 mg, 11.9% yield) was isolated as a colorless oil. LRMS (ESI): calc. 304.2; found 305.3 (MH)+.

Workup

  1. customThe residue was purified via ISCO flash chromatography (5% to 35% EtOAc/Hexane; 40G column)

Sources & evidence

ORD record
ord-356091b7930946ca86228c4b7ba1c7ab
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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