Triphenylphosphine → Methyl 3-amino-1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]indazole-5-carboxylate

HRID 2203183Notes

Reaction equation

HRID 2203183 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:11]O)[CH:10]=1)[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:6]=[CH:5]2.[NH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[NH:20][N:19]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[NH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=2)[N:20]([CH2:11][C:9]2[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:8]=2[N:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[N:6]=[CH:5]3)[N:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 84663082methyl 3-amino-1H-indazole-5-carboxylateHCID 118251601(5-Chloro-1-isobutyl-1H-indazole-7-yl)-methanol

Product 1

HCID 118251621Methyl 3-amino-1-[(5-chloro-1-isobutyl-indazol-7-yl)methyl]indazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of compound 17 (0.112 g, 0.47 mmol), methyl 3-amino-1H-indazole-5-carboxylate (0.075 g, 0.39 mmol), di-tert-butyl azocarboxylate (0.135 g, 0.59 mmol), triphenylphosphine (0.155 g, 0.59 mmol), in tetrahydrofuran (4 mL) was heated at 140° C. under microwave conditions for 20 minutes. Then, the reaction was quenched by adding water and diluted with ethyl acetate. The organic layer was separated, washed with Brine, dried (MgSO4), filtered and the solvent was evaporated. Then, the residue was purified by chromatography column on a 20 g SPE cartridge to give the title compound as a colorless solid. (0.090 g, 56%)

Workup

  1. customThen, the reaction was quenched
  2. additionby adding water
  3. additiondiluted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with Brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThen, the residue was purified by chromatography column on a 20 g SPE cartridge

Sources & evidence

ORD record
ord-bd7ee3c4db5f4da1adfc5cffe29b15aa
Source dataset
uspto-grants-2016_06
Patent number
US09365569B2

Reaction notes

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