Sodium Carbonate → HCID 131735902, compound

HRID 2207389Notes

Reaction equation

HRID 2207389 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=2)[CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.[Br:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33](Br)[CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:28][C:29]1[CH:34]=[C:33]([C:6]2[CH:5]=[C:4]([NH:17][C:18]3[N:23]=[C:22]([C:24]([F:25])([F:26])[F:27])[CH:21]=[CH:20][N:19]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=2)[CH:32]=[N:31][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 58456089N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 131735902HCID 131735902, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (2.00 g, 5.27 mmol), 3,5-dibromopyridine (4.37 g, 18.5 mmol) and Pd(dppf)Cl2—CH2Cl2 (0.215 g, 0.264 mmol) in 1,4-dioxane (26.4 mL, 0.2 M), and Na2CO3 (5.27 mL, 2.00 M) was purged with argon and heated to 80° C. for 4 hours. The reaction mixture was filtered through a CELITE plug and washed with dichloromethane. The eluent was diluted with water and extracted with dichloromethane (3×). The combined organic layers were concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford N-[3-(5-bromopyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine. MS APCI calc'd for C17H13BrF3N4 [M+H]+ 409 and 411. found 409 and 411.

Workup

  1. customwas purged with argon
  2. filtrationThe reaction mixture was filtered through a CELITE plug
  3. washwashed with dichloromethane
  4. additionThe eluent was diluted with water
  5. extractionextracted with dichloromethane (3×)
  6. concentrationThe combined organic layers were concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9c954620ead941caa460826e93f84e2c
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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