HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Potassium Carbonate → 3-(4-Amino-2-fluorophenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 1428113
Notes
Print preview

Reaction equation

HRID 1428113 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:15])=[N:10][CH:11]=[C:12](Br)[CH:13]=2)=[C:4]([F:16])[CH:3]=1.[CH3:17][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>O1CCOCC1.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>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:15])=[N:10][CH:11]=[C:12]([C:21]3[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=3)[CH:13]=2)=[C:4]([F:16])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 867000473-(4-Amino-2-fluorophenyl)-5-bromopyridin-2-amine

Product 1

HCID 867000663-(4-Amino-2-fluorophenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amineYield 93.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

The compound obtained in Step 1 of Example 29 (2 g), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.62 g), tetrakis(triphenylphosphine)palladium (0.41 g) and potassium carbonate (2.94 g) were suspended in dioxane (10 ml) and water (1 ml), and the suspension was heated under reflux at 100° C. for 61 hours. After leaving to cool, a saturated aqueous sodium bicarbonate solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate:methanol=10:1 (v/v)] to give 1.88 g of the title compound as a solid.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. extractionthe organic layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [ethyl acetate:methanol=10:1 (v/v)]

Sources & evidence

ORD record
ord-6a3901e1b5454e9eaf582417589f766f
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933103B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes