Potassium Carbonate → HCID 86653031, compound

HRID 1948723Notes

Reaction equation

HRID 1948723 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[S:15]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16]1.C([O-])([O-])=O.[K+].[K+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:17]1[CH:18]=[CH:19][S:15][CH:16]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 6890822-Chloro-8-methylquinoline-3-carboxaldehyde

Product 1

HCID 86653031HCID 86653031, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro-8-methylquinoline-3-carboxaldehyde (258 mg, 1.26 mmol), 3-thiopheneboronic acid (193 mg, 1.51 mmol), K2CO3 (260 mg, 1.88 mmol), palladium(II) acetate (5.6 mg, 0.025 mmol) and triphenylphosphine (26.3 mg, 0.10 mmol) in water (2 mL) was degassed. 1,4-Dioxane (6 mL) was added and the mixture further degassed, then heated at 100° C. for 1 h under microwave irradiation. The reaction mixture was diluted with DCM (30 mL) and water (10 mL). The organic layer was separated, dried (MgSO4) and concentrated in vacuo. Purification by column chromatography (SiO2, 10% EtOAc in heptane) gave the title compound (297 mg, 93%) as a colourless crystalline solid. δH (CDCl3) 10.40 (s, 1H), 8.75 (s, 1H), 7.83 (d, J 9 Hz, 1H), 7.60-7.73 (m, 3H), 7.46-7.54 (m, 2H), 2.85 (s, 3H). LCMS (ES+) 254.2 (M+H)+, RT 4.29 minutes (Method 3).

Workup

  1. customwas degassed
  2. addition1,4-Dioxane (6 mL) was added
  3. additionThe reaction mixture was diluted with DCM (30 mL) and water (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by column chromatography (SiO2, 10% EtOAc in heptane)

Sources & evidence

ORD record
ord-2fb663d4167c43458c421d163d66f6fc
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

Loading…