Ethyl Acetate → HCID 131731044, compound

HRID 2042095Notes

Reaction equation

HRID 2042095 reaction equation
N[C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([C:16]([O:18][C:19](C)([CH3:21])C)=[O:17])[N:11]=[CH:10]3)[N:5]=[C:4]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:3]=1.[C:27](Cl)([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28].C([O-])(O)=O.[Na+].[CH3:41][CH2:42]OC(C)=O>>[C:23]([C:4]1[CH:3]=[C:2]([C:27]([O:29][CH2:30][C:31]([Cl:34])([Cl:33])[Cl:32])=[O:28])[N:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([C:16]([O:18][CH2:19][CH2:21][CH2:41][CH3:42])=[O:17])[N:11]=[CH:10]3)[N:5]=1)([CH3:25])([CH3:26])[CH3:24]

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 67253077HCID 67253077, compound

Product 1

HCID 131731044HCID 131731044, compoundYield 97%

Procedure

To a stirring suspension of tert-butyl 5-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)-1H-indazole-1-carboxylate (see WO 2006/071940A2, 0.250 g, 0.70 mmol) and Troc-Cl (0.10 ml, 0.74 mmol) in EtOAc (7 ml) at RT was added sat'd. NaHCO3 (2.9 ml, 2.1 mmol). After 3 h, the completed reaction was diluted with hexanes (35 ml) and filtered. The solid was rinsed well with hexanes and dried to afford tent-butyl 5-(3-tert-butyl-5-((2,2,2-trichloroethoxy)carbonyl)-1H-pyrazol-1-yl)-1H-indazole-1-carboxylate (0.36 g, 97% yield). MS (ESI) m/z: 532.0 (M+H+).

Workup

  1. additionwas added
  2. customthe completed reaction
  3. filtrationfiltered
  4. washThe solid was rinsed well with hexanes
  5. customdried

Sources & evidence

ORD record
ord-e13b647ec9084e9a97cc9708c01276e0
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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