Cesium carbonate → HCID 67271616, compound

HRID 1696474Notes

Reaction equation

HRID 1696474 reaction equation
Cl.Br[C:3]1[CH:4]=[C:5]([N:9]2[C:13]([NH2:14])=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.CC1(C)C(C)(C)OB([C:27]2[CH:28]=[N:29][N:30](C(OC(C)(C)C)=O)[CH:31]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[NH:29]1[CH:28]=[C:27]([C:3]2[CH:4]=[C:5]([N:9]3[C:13]([NH2:14])=[CH:12][C:11]([C:15]([CH3:18])([CH3:17])[CH3:16])=[N:10]3)[CH:6]=[CH:7][CH:8]=2)[CH:31]=[N:30]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 534073321-(3-Bromophenyl)-3-tert-butyl-1H-pyrazol-5-amine--hydrogen chloride (1/1)

Product 1

HCID 67271616HCID 67271616, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-(3-bromophenyl)-3-t-butyl-1H-pyrazol-5-amine hydrochloride (0.253 g, 0.77 mmol, available from Example 54), t-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (0.28 g, 0.95 mmol, commercially available) and Cs2CO3 (1.0 g, 3.1 mmol) in DMF (5 mL) and H2O (2 mL) was placed under Ar for 15 min. Palladium tetrakis(triphenylphosphine) was added and the reaction mixture was heated at 80° C. overnight. The reaction mixture was poured into H2O (20 mL) and extracted with EtOAc (2×30 mL). The extracts were washed with H2O (10 mL) and brine (10 mL), dried (Na2SO4) concentrated and purified via column chromatography to yield 1-(3-(1H-pyrazol-4-yl)phenyl)-3-t-butyl-1H-pyrazol-5-amine (163 mg, 76% yield). MS (ESI) m/z: 282.3 (M+H+).

Workup

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe extracts were washed with H2O (10 mL) and brine (10 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-4babff8357594ae2a7b19f34bf0b8bd3
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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