3-Amino-5-bromopyridine → HCID 131735903, compound

HRID 2207391Notes

Reaction equation

HRID 2207391 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[C:29]1[CH:30]=[C:31]([NH2:35])[CH:32]=[N:33][CH:34]=1>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+].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>[NH2:35][C:31]1[CH:30]=[C:29]([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:34]=[N:33][CH:32]=1

Participants

6

Reactant 2

HCID 8176813-Amino-5-bromopyridineHCID 58456089N-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 131735903HCID 131735903, compound

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 10340Sodium CarbonateSolventHCID 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 (4.00 g, 10.6 mmol), 5-bromopyridin-3-amine (2.01 g, 11.6 mmol), Pd(dppf)Cl2—CH2Cl2 (0.431 g, 0.527 mmol) in 1,4-dioxane (52.7 mL, 0.2 M) and Na2CO3 (10.6 mL, 2 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 purified by silica gel column chromatography (methanol/ethyl acetate) to afford N-[3-(5-aminopyridin-3-yl)-5-methylphenyl]-4-(trifluoromethyl)pyrimidin-2-amine. MS APCI calc'd for C17H15F3N5 [M+H]+ 346. found 346.

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. custompurified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-1009c044d6a34f3a9726640620d41ae9
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

Loading…