Water → HCID 66876652, compound

HRID 1620032Notes

Reaction equation

HRID 1620032 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][C:5]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:15])[CH:3]=1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][C:22](B(O)O)=[CH:23][CH:24]=2)[CH:19]=[N:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[N:17]([CH3:16])[N:18]=[CH:19]3)=[CH:6][C:5]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:15])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 225589101-Methyl-1H-indazole-5-boronic acidHCID 66876970HCID 66876970, compound

Product 1

HCID 66876652HCID 66876652, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Intermediate 9 (460 mg) in 1,4-dioxane (5 ml, KANTO) was added with 1-methyl-1H-indazol-5-ylboronic acid (rgt1, 350 mg), cesium carbonate (410 mg, KANTO), and PdCl2dppf·CH2Cl2 (115 mg, Ald), and stirred at 90° C. for 18 hours. The reaction mixture was cooled to room temperature, and then added with water (30 ml) and ethyl acetate (30 ml×2) to perform extraction. The reaction mixture was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine, the organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1), and the solvent was evaporated under reduced pressure by using a rotary evaporator to obtain the title compound (400 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextraction
  3. washThe reaction mixture was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  4. customthe organic layer was dried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)
  7. customthe solvent was evaporated under reduced pressure
  8. customa rotary evaporator

Sources & evidence

ORD record
ord-fe9438a3369d43d995cb775e23f8b57b
Source dataset
uspto-grants-2014_07
Patent number
US08772327B2

Reaction notes

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