Aniline → HCID 90408929, compound

HRID 2177642Notes

Reaction equation

HRID 2177642 reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Cl[C:48]1[CH:53]=[C:52]([CH3:54])[N:51]=[C:50]([CH3:55])[C:49]=1[N+:56]([O-])=O.ClC1C=C[N:63]=CC=1[N+]([O-])=O.[NH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1.NC1C=CC=CN=1.[H-].[Na+].C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1.C1COCC1>[CH3:55][C:50]1[C:49]2[N:56]=[N:63][N:69]([C:70]3[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=3)[C:48]=2[CH:53]=[C:52]([CH3:54])[N:51]=1

Participants

11

Reactant 7

HCID 6115AnilineHCID 104392-AminopyridineHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 634876Binap, (A+-)-HCID 27357814-Chloro-3-nitropyridineHCID 107027254-Chloro-2,6-dimethyl-3-nitropyridine

Product 1

HCID 90408929HCID 90408929, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in a manner analogous to Intermediate 17, Step 1 through Intermediate 19, Step 3. In the synthesis of Intermediate 17, Step 1 Pd(OAc)2 and BINAP were eliminated and these substitutions were made: 4-chloro-2,6-dimethyl-3-nitropyridine for 4-chloro-3-nitropyridine, aniline for 2-aminopyridine, NaH for K2CO3, and THF for toluene, and the reaction was carried out for 24 h at room temperature. MS (ESI) mass calcd. C13H12N4, 224.1. m/z found, 225.1 [M+H]+.

Sources & evidence

ORD record
ord-f4e48d0dd992451e8ba820eac17b4beb
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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