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

4-Formylphenylboronic Acid → 7-Chloro-2-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile

HRID 1178624
Notes
Print preview

Reaction equation

HRID 1178624 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[C:11](I)[S:12][C:3]=12.[CH:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15]>COCCOC.C(=O)(O)[O-].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[C:11]([C:19]3[CH:20]=[CH:21][C:16]([CH:14]=[O:15])=[CH:17][CH:18]=3)[S:12][C:3]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 5910734-Formylphenylboronic AcidHCID 99961437-Chloro-2-iodothieno[3,2-B]pyridine-6-carbonitrile

Product 1

HCID 114607457-Chloro-2-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrileYield 87.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8071
1,2-Dimethoxyethane
Solvent
HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 7-chloro-2-iodo-thieno[3,2-b]pyridine-6-carbonitrile (1.00 g, 3.12 mmol), 4-formylphenylboronic acid (936 mg, 6.24 mmol) and 108 mgs of tetrakis(triphenylphosphine)palladium (0) in 30 mL of ethylene glycol dimethyl ether and 25 mL of aqueous saturated sodium bicarbonate is heated at reflux for 4 hours. The mixture is cooled and the precipitate is collected by filtration washing with ethyl acetate and diethyl ether to provide 818 mg of 7-chloro-2-(4-formylphenyl)thieno[3,2-b]pyridine-6-carbonitrile as a yellow solid, mp 300–305° C.; 1H NMR (CDCl3) δ 7.93 (d, J=8 Hz, 2H), 7.96 (s, 1H), 8.03 (d, J=8 Hz, 2H), 8.87 (s, 1H), 10.1 (s, 1H), MS 298.0, 300.0 (M−H)−H.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture is cooled
  4. filtrationthe precipitate is collected by filtration
  5. washwashing with ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-070c3513dbf649dc9662c13984c185d4
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07276519B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes