Potassium Carbonate → 6-(4-Formylbenzo[b]thiophen-7-yloxy)nicotinonitrile

HRID 2060878Notes

Reaction equation

[OH:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5]([CH:11]=[O:12])=[CH:4][CH:3]=1.Cl[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>S1(CCCC1)(=O)=O>[CH:11]([C:5]1[C:6]2[CH:10]=[CH:9][S:8][C:7]=2[C:2]([O:1][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=2)=[CH:3][CH:4]=1)=[O:12]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 7-hydroxybenzo[b]thiophene-4-carbaldehyde (Preparation 69) (100 mg, 0.62 mmol), 6-chloronicotinonitrile (86 mg, 0.62 mmol) and K2CO3 (258 mg, 1.87 mmol) in sulfolane (3 mL) was heated in a microwave reactor at 130 W/80° C. for 4 h. The mixture was cooled, poured onto ice water and the resulting solid filtered and air-dried to give the title compound: RT=3.40 min; m/z (ES+)=265.2 [M+H]+.

Workup

temperatureThe mixture was cooled
additionpoured onto ice water
filtrationthe resulting solid filtered
customair-dried

Sources & evidence

ORD record: ord-11d83db49da44793b4e419b4065382ca
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278442B2

Reaction notes

Loading…