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

Ethanol → 3-(4-Fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid ethyl ester

HRID 1423013
Notes
Print preview

Reaction equation

HRID 1423013 reaction equation
Br[C:2]1[C:3]2[N:4]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.CCN([CH2:23][CH3:24])CC.[C]=[O:26].[CH2:27]([OH:29])C>[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2]>[CH2:23]([O:26][C:27]([C:2]1[C:3]2[N:4]([C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:29])[CH3:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 671955508-Bromo-3-(4-fluorophenyl)-imidazo[1,5-a]pyridineHCID 178418416HCID 178418416, compound

Product 1

HCID 683454063-(4-Fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 15241612
1,1`-Bis(diphenylphosphino)ferrocene
Catalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 8-bromo-3-(4-fluorophenyl)-imidazo[1,5-a]pyridine (355 mg, 1.22 mmol), Et3N (330 μL, 2.5 mmol), Pd[PhCN]2Cl2 (11 mg, 0.029 mmol), and 1,1-bis(diphenylphosphino)ferrocene (dppf) (42 mg, 0.076 mmol) in absolute ethanol (15 mL) is placed in a pressure reactor with stirring and placed under 15 bars of carbon monoxide and warmed at 140° C. After 4 hours, the pressure reactor is cooled to room temperature, returned to atmospheric pressure and opened. The reaction mixture is concentrated in vacuo, the resulting residue is dissolved in dichloromethane and passed through a pad of silica gel eluting with ethyl ether to afford 3-(4-fluorophenyl)-imidazo[1,5-a]pyridine-8-carboxylic acid ethyl ester.

Workup

  1. customis placed in a pressure reactor
  2. temperaturethe pressure reactor is cooled to room temperature
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. dissolutionthe resulting residue is dissolved in dichloromethane

Sources & evidence

ORD record
ord-45eef0d15f8d441a87d2bf10e7d2cd84
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927550B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes