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

Potassium Carbonate → 1-(3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole

HRID 1699192
Notes
Print preview

Reaction equation

HRID 1699192 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([Cl:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]1[CH:22]=[N:23][C:24](/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[CH:25][CH:26]=1.CS(Cl)(=O)=O.[Br:41][C:42]1[N:46]2[CH:47]=[CH:48][CH:49]=[C:50](O)[C:45]2=[N:44][C:43]=1[CH3:52].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(N(CC)CC)C>[Br:41][C:42]1[N:46]2[CH:47]=[CH:48][CH:49]=[C:50]([O:9][CH2:8][C:7]3[C:2]([Cl:1])=[C:3]([N:11]4[CH:15]=[CH:14][CH:13]=[C:12]4[CH2:16][NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]4[CH:22]=[N:23][C:24](/[CH:27]=[CH:28]/[C:29]5[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=5)=[CH:25][CH:26]=4)[CH:4]=[CH:5][C:6]=3[Cl:10])[C:45]2=[N:44][C:43]=1[CH3:52]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 183218891-(2,4-dichloro-3-hydroxymethylphenyl)-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrroleHCID 183219553-Bromo-8-hydroxy-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 70255217
1-(3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole
Yield 76.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole (70 mg) and triethylamine (28 mg) in N,N-dimethylformamide (1 ml) was added methanesulfonyl chloride (16.7 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. To the mixture were added 3-bromo-8-hydroxy-2-methylimidazo[1,2-a]pyridine (31.4 mg) and potassium carbonate (95.7 mg) at ambient temperature, and the mixture was stirred at the same temperature overnight. Water was added thereto, the resulting precipitates were collected by filtration. The residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V) to give 1-(3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole (76 mg) as yellow amorphous.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature overnight
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V)

Sources & evidence

ORD record
ord-73c1433367d54f44b27f82d6434b7fcc
Source dataset
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06344462B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes