Ammonia → 3-(tert-butyl)-1-(1-methyl-1H-indol-5-yl)-1H-pyrazol-5-amine

HRID 594202Notes

Reaction equation

HRID 594202 reaction equation
CN(C)C=O.[NH2:6][C:7]1[CH:11]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[NH:9][N:8]=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]=[CH:18]1.N>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.N1C=CC=CC=1>[C:12]([C:10]1[CH:11]=[C:7]([NH2:6])[N:8]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[N:17]([CH3:16])[CH:18]=[CH:19]3)[N:9]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 5227873-Amino-5-tert-butylpyrazoleHCID 27598671-Methyl-1H-indole-5-boronic acid

Product 1

HCID 1179216833-(tert-butyl)-1-(1-methyl-1H-indol-5-yl)-1H-pyrazol-5-amineYield 48.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 1049PyridineSolvent

Procedure

To a mixed solvent of dimethylformamide (8 mL) and pyridine (0.47 mL) were added 3-amino-5-tert-butylpyrazole (810 mg), N-methylindol-5-boronic acid (780 mg), copper (II) acetate (790 mg) and molecular sieves (400 mg). The reaction mixture was stirred overnight at room temperature. The reaction mixture was added with 10% aqueous ammonia and filtered through Celite®. The filtrate was added with ethyl acetate and separated. The obtained organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=7:3→1:1→1:4) to give the titled compound (577 mg) having the following physical data.

Workup

  1. filtrationfiltered through Celite®
  2. additionThe filtrate was added with ethyl acetate
  3. customseparated
  4. washThe obtained organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe obtained residue was purified on silica gel column chromatography (hexane:ethyl acetate=7:3→1:1→1:4)

Sources & evidence

ORD record
ord-b2a73516c8834a8d8cfd3d9e5b650e87
Source dataset
uspto-grants-2016_01
Patent number
US09242977B2

Reaction notes

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