Triethylamine → 5-(1-Benzenesulfonyl-7-fluoroindol-3-yl)-thiophene-2-carboxaldehyde

HRID 644072Notes

Reaction equation

HRID 644072 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:19])[C:12](Br)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([C:23]1[S:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].C(N(CC)CC)C>C(O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:19])[C:12]([C:26]3[S:27][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27734305-Formyl-2-thiopheneboronic acidHCID 596035291-benzenesulfonyl-3-bromo-7-fluoro-1H-indole

Product 1

HCID 860732925-(1-Benzenesulfonyl-7-fluoroindol-3-yl)-thiophene-2-carboxaldehydeYield 77.3%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzenesulfonyl-3-bromo-7-fluoroindole (0.5 g, 1.41 mmol), 5-formyl-2-thiophene boronic acid (0.24 g, 1.55 mmol), bis(triphenylphosphine) palladium (II) dichloride (0.06 g, 0.08 mmol) and triethylamine (0.39 ml, 2.82 mmol) in ethanol (4 ml) was subjected to microwave irradiation at 150° C. for 420 s. The resulting suspension was concentrated under reduced pressure and the residue passed through a silica pad eluting with dichloromethane to afford crude 5-(1-benzenesulfonyl-7-fluoroindol-3-yl)-thiophene-2-carboxaldehyde as a brown solid (0.42 g) which was used in the next step with no further purification.

Workup

  1. customirradiation at 150° C. for 420 s
  2. concentrationThe resulting suspension was concentrated under reduced pressure
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-095010febf2f47b587cb51c8dfe3d52b
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

Loading…