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Methanol → N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)methanesulfonamide

HRID 1477861
Notes
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Reaction equation

HRID 1477861 reaction equation
[Li+].[BH4-].CO.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:19]2[C:27]3[C:22](=[C:23]([N:28](COCC[Si](C)(C)C)[S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[N:20]2)([CH2:17][CH3:18])[C:13](OC)=O)=[CH:8][CH:7]=1>C1COCC1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([N:19]2[C:27]3[C:22](=[C:23]([NH:28][S:29]([CH3:32])(=[O:30])=[O:31])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[N:20]2)([CH:13]2[CH2:8][CH:9]2[C:12]#[N:19])[CH2:17][CH3:18])=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 70565947methyl 2-(4-chlorophenyl)-2-(4-(N-((2-(trimethylsilyl)ethoxy)methyl)methylsulfonamido)-1H-indazol-1-yl)butanoate

Product 1

HCID 57524237N-(1-(1-(4-chlorophenyl)-1-(2-cyanocyclopropyl)propyl)-1H-indazol-4-yl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a suspension of LiBH4 (120 mg, 5.43 mmol) in THF (5 mL) was added MeOH (174 mg, 5.43 mmol) and a solution of methyl 2-(4-chlorophenyl)-2-(4-(N-((2-(trimethylsilyl)ethoxy)methyl)methylsulfonamido)-1H-indazol-1-yl)butanoate (600 mg, 1.09 mmol) in THF (8 mL) followed. The mixture was stirred at room temperature for 2 h. The solution was quenched with saturated NH4Cl solution, and extracted with ethyl acetate (30 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (PE/EA=3/1) to afford the title compound as a pale yellow solid. LC/MS m/z=524.2 [M+H]+.

Workup

  1. customThe solution was quenched with saturated NH4Cl solution
  2. extractionextracted with ethyl acetate (30 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography (PE/EA=3/1)

Sources & evidence

ORD record
ord-880d68830cc04dd8b8f0c3cd973bfa47
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09403807B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes