Sodium Carbonate → 3-(1H-imidazo[4,5-b]pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine

HRID 241413Notes

Reaction equation

HRID 241413 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:12]([N:17]=2)=[N:13][CH:14]=[CH:15][CH:16]=3)[C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:10]1[C:11]2[C:12](=[N:13][CH:14]=[CH:15][CH:16]=2)[N:17]=[C:9]1[C:4]1[C:5]([NH2:8])=[N:6][CH:7]=[C:2]([C:22]2[CH:21]=[N:20][N:19]([CH3:18])[CH:23]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 668698105-bromo-3-(1H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-ylamine

Product 1

HCID 668985513-(1H-imidazo[4,5-b]pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

58 mg (0.200 mmol) of 5-bromo-3-(1H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-ylamine and 45.8 mg (0.220 mmol) of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole are suspended in 2 ml of N,N-dimethylformamide in a nitrogen-filled microwave vessel, and 0.57 ml (1.142 mmol) of 2M sodium carbonate solution and 23.1 mg (0.020 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer. The reaction mixture is evaporated to dryness, and the residue is purified by means of RP-HPLC, giving 3-(1H-imidazo[4,5-b]pyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-ylamine; HPLC-MS [M+H]+ 292.2;

Workup

  1. additionfilled microwave vessel
  2. customThe reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer
  3. customThe reaction mixture is evaporated to dryness
  4. customthe residue is purified by means of RP-HPLC

Sources & evidence

ORD record
ord-a1ef29d4a7fb4ec281e9f0fd034bb37c
Source dataset
uspto-grants-2014_02
Patent number
US08648201B2

Reaction notes

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