Triphenylphosphine → 4-Aminofuro[3,2-c]pyridine-2-carbonitrile

HRID 1008554Notes

Reaction equation

HRID 1008554 reaction equation
I[C:2]1[O:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH2:11])[C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:31][C:32]1C2C(=CC=C(C#N)C=2)C=CN=1>CN1CCCC1=O.[C-]#N.[Zn+2].[C-]#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:11][C:5]1[C:4]2[CH:3]=[C:2]([C:32]#[N:31])[O:10][C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 226658481-Aminoisoquinoline-7-carbonitrileHCID 226659052-Iodofuro[3,2-c]pyridin-4-amine

Product 1

HCID 226658084-Aminofuro[3,2-c]pyridine-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 167845palladium(II) acetateCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

This compound was prepared from 2-iodo-furo[3,2-c]pyridin-4-ylamine (5.2 g), zinc cyanide (3.6 g), triphenylphosphine (2.1 g) and palladium acetate (1.8 g) in 75 mL of N-methyl-pyrrolidone using the procedure described for 1-amino-isoquinoline-7-carbonitrile. Yield: 2.0 g (64%); yellow solid; m.p. 280° C. (decomp.).

Sources & evidence

ORD record
ord-02c74e5de15a42509fc99605080e48f0
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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