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Isopropyl chloroformate → 5-[1-(1-Methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-hydroxyethyl]indazole-1-carboxylic acid isopropyl ester

HRID 244419
Notes
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Reaction equation

HRID 244419 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][N:19]=[CH:18]2)([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH3:14])[CH:6]=1)[OH:4].Cl[C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28]>C1(C)C=CC=CC=1.N1C=CC=CC=1.CCOCC.O>[CH:30]([O:29][C:27]([N:20]1[C:21]2[C:17](=[CH:16][C:15]([C:3]([C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[N:7]([CH3:14])[CH:6]=3)([OH:4])[C:2]([F:1])([F:24])[F:25])=[CH:23][CH:22]=2)[CH:18]=[N:19]1)=[O:28])([CH3:32])[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 7917Isopropyl chloroformateHCID 594372242,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol

Product 1

HCID 594372315-[1-(1-Methyl-1H-indol-3-yl)-2,2,2-trifluoro-1-hydroxyethyl]indazole-1-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049Pyridine
Solvent
HCID 1140TolueneSolvent
HCID 3283Diethyl EtherSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol (0.165 mmol) and isopropyl chloroformate (0.49 mmol from a 1.0 M solution in toluene) in 1 mL of pyridine was heated at 85° C. for 10 hours, cooled to room temperature, and diluted with ether and water. The organic layer was washed with water and brine and dried over magnesium sulfate. The volatiles were concentrated in vacuo and the residue purified by flash silica gel chromatography using 33% ethyl acetate in hexanes. The product-rich fractions were concentrated in vacuo to afford 0.069 mmol of the desired compound, m.p. 105° C.-106° C.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe volatiles were concentrated in vacuo
  5. customthe residue purified by flash silica gel chromatography
  6. concentrationThe product-rich fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-4f6c81ff658b4ff0aca55d9b1ba68360
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658637B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes