Sodium Carbonate → HCID 16222983, compound

HRID 1505634Notes

Reaction equation

HRID 1505634 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]2[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:16][S:17][C:13]=2[C:12](Br)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([NH:8][C:9]1[C:14]2[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)=[CH:16][S:17][C:13]=2[C:12]([C:30]2[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=2)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 79799Tolylboronic acidHCID 66671334HCID 66671334, compound

Product 1

HCID 16222983HCID 16222983, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
150 °C

Procedure

A microwave reaction vessel was charged with benzyl-(7-bromo-3-p-tolyl-thieno[3,2-c]pyridin-4-yl)amine (20.0 mg, 0.0489 mmol), 4-methylphenylboronic acid (6.6 mg, 0.0489 mmol), palladium (II) acetate (1.0 mg, 0.00489 mmol), triphenylphosphine (3.8 mg, 0.0147 mmol) and sodium carbonate (15.5 mg, 0.147 mmol). The reaction was solvated in DME (0.75 ml) and distilled water (0.25 ml), the tube sealed, and set to stir in a Biotage microwave reactor. The reaction was heated at 150° C. for 1 h. At which point the reaction was allowed to cool to room temperature and further diluted with distilled water (10 ml). The aqueous phase was then extracted with DCM (2×20 ml), dried (MgSO4), filtered and the solvent removed in vacuo. The crude residue was subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 10:1, Rf 0.3). This afforded the title compound as a yellow solid (11.0 mg, 53%).

Workup

  1. customA microwave reaction vessel
  2. distillationdistilled water (0.25 ml)
  3. customthe tube sealed
  4. temperatureto cool to room temperature
  5. additionfurther diluted with distilled water (10 ml)
  6. extractionThe aqueous phase was then extracted with DCM (2×20 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed in vacuo
  10. customwas subjected to flash column chromatography (eluent petroleum spirit 40-60° C.:EtOAc, 10:1, Rf 0.3)

Sources & evidence

ORD record
ord-a6e162c4da9441fd90218324acadb6af
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

Loading…