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Benzoyl chloride → Phenyl-{5-[2,2,2-trifluoro-1-hydroxy-1-(1-methyl-1H-indol-3-yl)ethyl]indazol-1-yl}methanone

HRID 244416
Notes
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Reaction equation

HRID 244416 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].[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>N1C=CC=CC=1.CCOCC.O>[C:27]1([C:26]([N:20]2[C:21]3[C:17](=[CH:16][C:15]([C:3]([OH:4])([C:5]4[C:13]5[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=5)[N:7]([CH3:14])[CH:6]=4)[C:2]([F:1])([F:24])[F:25])=[CH:23][CH:22]=3)[CH:18]=[N:19]2)=[O:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 594372242,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol

Product 1

HCID 59437295Phenyl-{5-[2,2,2-trifluoro-1-hydroxy-1-(1-methyl-1H-indol-3-yl)ethyl]indazol-1-yl}methanoneYield 57.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049
Pyridine
Solvent
HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol (0.162 mmol) and benzoyl chloride (0.324 mmol) in 1 mL pyridine was heated at 100° C. After 2 hours, the mixture was cooled to room temperature and diluted with ether and water. The organic layer was washed with aqueous HCl and brine and dried over magnesium sulfate. The volatiles were removed 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 provide 0.093 mmol of the title compound, m.p. 102° C.-103° C.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. washThe organic layer was washed with aqueous HCl and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe volatiles were removed 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-9b342229bb9b4af99ec8604f724d6e34
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