Water → HCID 10049176, compound

HRID 1611551Notes

Reaction equation

HRID 1611551 reaction equation
I[C:2]1[S:10][C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:24]#[N:25])[C:8]=2[NH:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH:3]=1.[CH:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)=[O:27].O>C(=O)(O)[O-].[Na+].COCCOC.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>[CH:26]([C:28]1[CH:33]=[CH:32][C:31]([C:2]2[S:10][C:9]3[C:4](=[N:5][CH:6]=[C:7]([C:24]#[N:25])[C:8]=3[NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[CH:3]=2)=[CH:30][CH:29]=1)=[O:27]

Participants

7

Reactant 3

HCID 962WaterHCID 5910734-Formylphenylboronic AcidHCID 10344502HCID 10344502, compound

Product 1

HCID 10049176HCID 10049176, compoundYield 93.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-iodo-7-[(3,4,5-trimethoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile (500 mg, 1.07 mmol), 4-formylphenylboronic acid (240.7 mg, 1.61 mmol), tetrakis(triphenylphosphine)palladium(0) (61.8 mg, 0.054 mmol) in 16 mL of saturated aqueous sodium bicarbonate and 20 mL of ethylene glycol dimethyl ether is heated at reflux for 3 h. After cooling, the mixture is treated with water. The precipitate is filtered, washed with water, ethyl acetate, and ether, then dried in vacuo to provide 447.2 mg of 2-(4-formylphenyl)-7-[(3,4,5-trimethoxyphenyl)amino]thieno[3,2-b]pyridine-6-carbonitrile as a yellow solid, mp 268-270° C.; 1H NMR (DMSO-d6) δ 3.73 (s, 3H), 3.75 (s, 6H), 6.69 (s, 2H), 7.94 (d, J=8 Hz, 2H), 8.00 (d, J=8 Hz, 2H), 8.10 (s, 1H), 8.64 (s, 1H), 9.64 (s, 1H), 10.00 (s, 1H); HRMS 446.11691 (M+H)+.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationThe precipitate is filtered
  5. washwashed with water, ethyl acetate, and ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-61a4cb0b6dea4be984c0b02a05aff4c2
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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