Potassium Carbonate → HCID 67453616, compound

HRID 869153Notes

Reaction equation

HRID 869153 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][CH2:9][C:10]2([C:14]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[C:28](B(O)O)=[CH:27][CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>O.C(OCC)(=O)C>[F:20][C:19]1[C:14]([C:10]2([CH2:9][NH:8][C:5]3[N:6]=[N:7][C:2]([C:28]4[C:23]([O:22][CH3:21])=[N:24][CH:25]=[CH:26][CH:27]=4)=[CH:3][CH:4]=3)[CH2:13][CH2:12][CH2:11]2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 86686129HCID 86686129, compound

Product 1

HCID 67453616HCID 67453616, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a 20 dram vial was added 6-chloro-N-((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)pyridazin-3-amine (1.8 g, 6.23 mmol, 1.0 equiv), 2-methoxypyridin-3-ylboronic acid (1.0 g, 6.54 mmol, 1.1 equiv), Cl2Pd(dppf) (350 mg, 0.43 mmol, 0.07 equiv), 2M potassium carbonate (8 mL, 15.5 mmol, 2.5 equiv), and dioxane (21 mL). The reaction was stirred and heated to 90° C. for 2 h and then diluted with water (20 mL) and ethyl acetate (50 mL). After transferring to a separatory funnel and shaking, the organic layer was separated from the aqueous layer and then washed with lithium chloride (1×20 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel column chromatography to give N-((1-(3-fluoropyridin-2-yl)cyclobutyl)methyl)-6-(2-methoxypyridin-3-yl)pyridazin-3-amine (1.7 g, 77%) as an off-white solid.

Workup

  1. customAfter transferring to a separatory funnel
  2. stirringshaking
  3. customthe organic layer was separated from the aqueous layer
  4. washwashed with lithium chloride (1×20 mL)
  5. dry with materialThe organic layer was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude solid that
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-227de07533e547b6962c3cd99a5d750b
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

Loading…