1,2-Dimethoxyethane → 2-Acetylamino-3-cyano-5-(4-cyanophenyl)thiophene

HRID 900446Notes

Reaction equation

HRID 900446 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7](Br)=[CH:8][C:9]=1[C:10]#[N:11])(=[O:3])[CH3:2].[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].C(=O)([O-])[O-].[K+].[K+].C(COC)OC>O>[C:1]([NH:4][C:5]1[S:6][C:7]([C:18]2[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=2)=[CH:8][C:9]=1[C:10]#[N:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 130528502-Acetylamino-5-bromo-3-cyanothiophene

Product 1

HCID 179309842-Acetylamino-3-cyano-5-(4-cyanophenyl)thiopheneYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Acetylamino-5-bromo-3-cyanothiophene (500 mg), 4-cyanophenylboronic acid (360 mg) and potassium carbonate (845 mg) were added to dimethoxyethane (15 ml) and water (2 ml) and the system purged with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (236 mg) was added and the mixture heated at 80° C. for 3.25 h. The mixture was cooled, concentrated under reduced pressure to remove most of the dimethoxymethane, dichloromethane added and the mixture filtered to give the product as a pale brown solid (470 mg).

Workup

  1. customthe system purged with argon for 15 minutes
  2. additionTetrakis(triphenylphosphine)palladium(0) (236 mg) was added
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customto remove most of the dimethoxymethane, dichloromethane
  6. additionadded
  7. filtrationthe mixture filtered

Sources & evidence

ORD record
ord-a2eb6bb84e6e47f0b713b54c043d71be
Source dataset
uspto-grants-2008_04
Patent number
US07358376B2

Reaction notes

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