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

HRID 1178624Notes

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

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, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 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
Patent number
US07276519B2

Reaction notes

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