Sodium Carbonate → 5-(1-Methyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 595847Notes

Reaction equation

HRID 595847 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:9][N:10]1[CH:14]=[C:13](B2OC(C)(C)C(C)(C)O2)[CH:12]=[N:11]1.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.COCCOC>[CH3:9][N:10]1[CH:14]=[C:13]([C:2]2[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)[CH:12]=[N:11]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 575128845-(1-Methyl-1H-pyrazol-4-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
115 °C

Procedure

To a microwave vial was charged 5-bromopyridin-2-amine (500 mg, 2.89 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.2 g, 5.78 mmol), aqueous Na2CO3 (2 M, 5.78 mL), PdCl2(dppf) CH2Cl2 (0.236 g) and DME (15 mL), and the reaction mixture was purged with Argon for 5 min, sealed and heated with microwave reactor at 115° C. for 20 min. The DME layer of reaction mixture was collected, concentrated and the residue was subjected to flash column chromatography on silica gel eluted with gradient Methanol/CH2Cl2 and 5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine was obtained as light brown solid (383 mg, 76% yield). LCMS (m/z): 175.2 (MH+), 0.34 min.

Workup

  1. customthe reaction mixture was purged with Argon for 5 min
  2. customsealed
  3. customThe DME layer of reaction mixture
  4. customwas collected
  5. concentrationconcentrated
  6. washeluted with gradient Methanol/CH2Cl2

Sources & evidence

ORD record
ord-fe9e55063a9a444da0997a26abdb6173
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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