Methanol → 5-(4-Aminophenylamino)-2-(2,6-difluorophenyl)oxazole-4-carbonitrile

HRID 389783Notes

Reaction equation

HRID 389783 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)=[C:12]([C:14]#[N:15])[N:13]=1.CO>[Pd].CCOC(C)=O>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:11]2[O:10][C:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[N:13][C:12]=2[C:14]#[N:15])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 595874302-(2,6-Difluorophenyl)-5-(4-nitrophenylamino)oxazole-4-carbonitrile

Product 1

HCID 595874505-(4-Aminophenylamino)-2-(2,6-difluorophenyl)oxazole-4-carbonitrileYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2,6-difluorophenyl)-5-(4-nitrophenylamino)oxazole-4-carbonitrile (0.435 g, 1.271 mmol) in 50:50 MeOH:EtOAc (10 ml) was hydrogenated using a 10% Pd/C catalyst at 30° C. at atmospheric pressure using the Thales H-Cube at a flow rate of 1 ml/min. The organic layer was then reduced in vacuo to yield 5-(4-aminophenylamino)-2-(2,6-difluorophenyl)oxazole-4-carbonitrile (0.360 g, 1.153 mmol, 90%). 1H NMR (CD3OD) δ 6.74 (2H, d), 7.10 (2H, d), 7.14 (2H, t), 7.55 (1H, m). LCMS (2) Rt: 2.47 min; m/z (ES+) 313.

Workup

  1. customat 30° C.

Sources & evidence

ORD record
ord-d3d6b9eb47ea4608baec933d76920b88
Source dataset
uspto-grants-2013_02
Patent number
US08378095B2

Reaction notes

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