Trichloroacetonitrile → HCID 66689988, compound

HRID 592321Notes

Reaction equation

HRID 592321 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7]=1[NH2:8].C1(P([C:33]2[CH:38]=[CH:37]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:40](Cl)(Cl)C#N>C(#N)C>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:6]2[C:7]3[N:8]=[C:40]([CH:38]([CH3:37])[CH3:33])[NH:1][C:2]=3[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 66690282HCID 66690282, compound

Product 1

HCID 66689988HCID 66689988, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of methyl 5,6-diamino-4′-fluorobiphenyl-3-carboxylate (0.19 g, 0.73 mmol) and solid support triphenylphosphine (75% by weight; 0.77 g, 2.2 mmol) in acetonitrile (2.4 mL) was added trichloroacetonitrile (0.15 mL, 1.46 mmol). The mixture was heated in a microwave reactor for 10 min at 150° C. The mixture was cooled to ambient temperature, filtered and concentrated. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (186 mg): LC-MS [M+1]=313.2.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-12e709434d0744dd9a6c16aaf3be4532
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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