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

Quinoline → 2-((R)-4-[1,3']Bipyrrolidinyl-1'-yl-3-fluorophenyl)-6-((Z)-pent-1-enyl)-2H-isoquinolin-1-one

HRID 69459
Notes
Print preview

Reaction equation

HRID 69459 reaction equation
[N:1]1([C@@H:6]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[C:22]([C:27]#[C:28][CH2:29][CH2:30][CH3:31])[CH:23]=5)[C:18]4=[O:32])=[CH:13][C:12]=3[F:33])[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C2C(=CC=CC=2)C=CC=1>[Pd].N1C=CC=CC=1>[N:1]1([C@@H:6]2[CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[C:22](/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH3:31])[CH:23]=5)[C:18]4=[O:32])=[CH:13][C:12]=3[F:33])[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7047QuinolineHCID 689933012-((R)-4-[1,3']bipyrrolidinyl-1'-yl-3-fluorophenyl)-6-pent-1-ynyl-2H-isoquinolin-1-one

Product 1

HCID 579166722-((R)-4-[1,3']Bipyrrolidinyl-1'-yl-3-fluorophenyl)-6-((Z)-pent-1-enyl)-2H-isoquinolin-1-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049Pyridine
Solvent

Procedure

A mixture of 2-((R)-4-[1,3′]bipyrrolidinyl-1′-yl-3-fluorophenyl)-6-pent-1-ynyl-2H-isoquinolin-1-one (2.7 g), quinoline (0.4 g), pyridine (50 mL) and palladium (5% on barium carbonate; 100 mg) was stirred vigorously for 2 hours under a hydrogen atmosphere (balloon flask). It was sucked off of the catalyst and the filtrate was concentrated. The residue was purified by chromatography on silica gel. In this way the product was obtained with molecular weight 445.59 (C28H32FN3O); MS (ESI): 446 (M+H+).

Workup

  1. concentrationthe filtrate was concentrated
  2. customThe residue was purified by chromatography on silica gel
  3. customIn this way the product was obtained with molecular weight 445.59 (C28H32FN3O)

Sources & evidence

ORD record
ord-029054dc99fa4911a8192d71569aa517
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822495B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes