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

Water → 6-Chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carbonitrile

HRID 2203343
Notes
Print preview

Reaction equation

HRID 2203343 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[N:9][C:10]=2I)[CH:7]=1.O.[CH3:22][N:23](C=O)C>[NH4+].[OH-].[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:12][CH2:13][C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])=[N:9][C:10]=2[C:22]#[N:23])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 866789786-Chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

Product 1

HCID 866789796-Chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carbonitrile

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst
HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the intermediate from Step H (4.32 g, 10.18 mmol) in DMF (50 mL) was added zinc cyanide (2.39 g, 20.35 mmol), Pd2 dba3 (0.47 g, 0.51 mmol), DPPF (0.564 g, 1.02 mmol), and water (2.5 mL). The resulting solution was heated at 120° C. for 18 hours. The reaction was cooled to room temperature, diluted with 15% NH4OH solution (10 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. m/z=323.9 (M+H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95459e3e17d343bc87e15af7dd127799
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365574B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes