Aniline → HCID 57445396, compound

HRID 1993357Notes

Reaction equation

HRID 1993357 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([F:16])[CH:9]=2)=[N:6][CH:7]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.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.CC([O-])(C)C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[F:16][C:10]1[CH:9]=[C:8]([C:5]2[N:4]=[CH:3][C:2]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:7][N:6]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

7

Reactant 4

HCID 6115AnilineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57445395HCID 57445395, compound

Product 1

HCID 57445396HCID 57445396, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a 50 mL round bottom flask under nitrogen was charged 5-bromo-2-(3-fluoro-4-methoxyphenyl)pyrimidine (Step 1, 0.40 g, 1.41 mmol), aniline (0.28 g, 3.0 mmol), Pd(OAc)2, (0.015 g, 0.067 mmol), BINAP (0.090 g, 0.064 mmol), and NaOtBu (0.27 g, 2.8 mmol). Toluene (5.0 mL) was added and the mixture was heated at 100° C. for 24 h. The mixture was cooled to RT and was partitioned between CH2Cl2 and H2O. The organic phase was dried over Na2SO4 and concentrated. Purification on silica with 1% MeOH in CH2Cl2 afforded the title compound as a purple solid. MS (ESI pos. ion) m/z: 296. Calc'd for C17H14FN3O: 295.11.

Workup

  1. temperatureThe mixture was cooled to RT
  2. customwas partitioned between CH2Cl2 and H2O
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification on silica with 1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-51b44f045bda4990ade449fa368d577c
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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