HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 244415
Notes
Print preview

Reaction equation

HRID 244415 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].[CH:26]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][CH2:27]1>N1C=CC=CC=1.CCOCC.O>[CH:26]1([C:30]([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:31])[CH2:29][CH2:28][CH2:27]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 594372242,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol

Product 1

HCID 59437314Cyclobutyl-{5-[2,2,2-trifluoro-1-hydroxy-1-(1-methyl-1H-indol-3-yl)ethyl]indazol-1-yl}methanoneYield 74.6%

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 (0.122 mmol) and cyclobutanecarbonyl chloride (0.159 mmol) in 1 mL pyridine was heated at 100° C. for 1.5 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 removed in vacuo and the residue purified by flash silica gel chromatography using 25% ethyl acetate in hexanes. The product-rich fractions were concentrated in vacuo to afford 0.091 mmol of the title compound, m.p. 79° C.-81° 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. 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-6210037021d74012865cf784ae8b15fc
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658637B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes