4-((Tert-butyldimethylsilyl)oxy)aniline → N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-cyclopropyl-1H-pyrazol-4-amine

HRID 515907Notes

Reaction equation

HRID 515907 reaction equation
[Si:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:17]1[CH:18]=[N:19][N:20]([CH:22]2[CH2:24][CH2:23]2)[CH:21]=1>O1CCCC1>[Si:1]([O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:17]2[CH:18]=[N:19][N:20]([CH:22]3[CH2:24][CH2:23]3)[CH:21]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 117155534-((Tert-butyldimethylsilyl)oxy)anilineHCID 521420994-Bromo-1-cyclopropyl-1H-pyrazole

Product 1

HCID 131733318N-(4-((tert-butyldimethylsilyl)oxy)phenyl)-1-cyclopropyl-1H-pyrazol-4-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[tert-Butyl(dimethyl)silyl]oxyaniline (1.64 g, 7.3 mmol) and 4-bromo-1-cyclopropyl-1H-pyrazole (1.4 g, 7.3 mmol) dissolved in anhydrous tetrahydrofuran (30 mL) are stirred for 3 hours at ambient temperature in the presence of sodium tert-butylate (3.7 mL, 2M solution in THF) and chloro(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) (101 mg, 0.146 mmol). The reaction mixture is filtered over Celite and then evaporated to dryness. The residue is purified by chromatography over silica gel using heptane and ethyl acetate as eluants to yield the expected product.

Workup

  1. filtrationThe reaction mixture is filtered over Celite
  2. customevaporated to dryness
  3. customThe residue is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-9df8a3390e4d442e9440eff5da724df8
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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