tert-butyl 1-(3-(4-chlorophenyl)-5,5,5-trifluoropent-1-yn-3-yl)-1H-indazol-4-ylcarbamate → tert-butyl 1-(3-(4-chlorophenyl)-1,1,1-trifluoropentan-3-yl)-1H-indazol-4-ylcarbamate

HRID 1477906Notes

Reaction equation

HRID 1477906 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH2:11][C:12]([F:15])([F:14])[F:13])[C:9]#[CH:10])=[CH:4][CH:3]=1>C(O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH2:9][CH3:10])[CH2:11][C:12]([F:14])([F:15])[F:13])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86705055tert-butyl 1-(3-(4-chlorophenyl)-5,5,5-trifluoropent-1-yn-3-yl)-1H-indazol-4-ylcarbamate

Product 1

HCID 70586827tert-butyl 1-(3-(4-chlorophenyl)-1,1,1-trifluoropentan-3-yl)-1H-indazol-4-ylcarbamate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product of Step D (100 mg, 0.21 mmol) in ethanol (3 mL) was added PtO2 (10 mg, 0.044 mmol) at room temperature under H2 atmosphere for 2 h. The solid was filtered off and filtrate was concentrated in vacuo to obtain the title compound as colorless oil. LC/MS m/z=468.1[M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationfiltrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c23c10f2806f4df9b33f729d76797b71
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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