Trichloroacetonitrile → HCID 59026763, compound

HRID 658368Notes

Reaction equation

HRID 658368 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=1[F:21])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)[C:44]#[N:45]>CC(N(C)C)=O>[F:21][C:15]1[CH:16]=[C:17]([I:20])[CH:18]=[CH:19][C:14]=1[NH:13][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:7]=1[C:6]1[O:22][C:1]([NH:45][CH3:44])=[N:4][N:5]=1

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 68826229HCID 68826229, compound

Product 1

HCID 59026763HCID 59026763, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid N′-acetyl-hydrazide (400 mg; 0.93 mmol; 1 eq) in DMA (5 mL), PS-Triphenyl-phosphine (1.22 g; 4.66 mmol; 5 eq), Trichloro-acetonitrile (269 mg; 1.86 mmol; 2 eq) and DIEPA (0.49 mL; 2.8 mmol; 3 eq) were added. The reaction mixture was stirred at 100° C. for 4 hrs. The mixture was filtered and the solution was subjected to preparative HPLC to afford the product (98 mg). LC/MS (Method A) [5.03 min; 412(M+1)]

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-bf6de54404fb46f39ce37c4d4ff81c88
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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