N-methyl-2-pyrrolidone → HCID 90177068, compound

HRID 919302Notes

Reaction equation

HRID 919302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1I.[CH3:10][N:11]1C(=O)CCC1>[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>[NH2:8][C:4]1[N:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:10]#[N:11]

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 229365964-Chloro-3-iodopyridin-2-amine

Product 1

HCID 90177068HCID 90177068, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
95 °C

Procedure

To a solution 4-chloro-3-iodopyridin-2-amine (200 mg, 0.79 mmol), Zn(CN)2 (46 mg, 0.39 mmol) in NMP (3 mL) was added Pd(PPh3)4 (136 mg, 0.12 mmol). The resulting mixture was allowed to stir at 95° C. under N2 for overnight. The reaction mixture was purified by column chromatography to afford the title compound as a white solid. LC/MS m/z=153.2 [M+H]+

Workup

  1. customThe reaction mixture was purified by column chromatography

Sources & evidence

ORD record
ord-dead9667bec34e5cbea7081243dd83d0
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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