Sodium Carbonate → HCID 16222777, compound

HRID 1505632Notes

Reaction equation

HRID 1505632 reaction equation
Br[C:2]1[C:6]2[C:7]([NH:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COCCOC>[C:19]1([C:2]2[C:6]3[C:7]([NH:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=4)=[N:8][CH:9]=[CH:10][C:5]=3[S:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 66671289HCID 66671289, compound

Product 1

HCID 16222777HCID 16222777, compoundYield 60%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
155 °C

Procedure

A microwave reaction vessel was charged with (3-bromo-thieno[3,2-c]pyridin-4-yl)-pyridin-2-ylmethyl-amine (50 mg, 0.158 mmol), phenylboronic acid (37.9 mg, 0.312 mmol), palladium (II) acetate (3.5 mg, 0.0158 mmol), triphenylphosphine (12.3 mg, 0.0467 mmol) and sodium carbonate (49.5 mg, 0.467 mmol). The reaction was solvated with DME (0.75 ml) and distilled water (0.25 ml), sealed, and set to stir in a Biotage microwave reactor. The reaction was heated at 150-160° 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, 1:1, Rf 0.1). This afforded the title compound as a yellow solid (29.8 mg, 60%).

Workup

  1. customA microwave reaction vessel
  2. distillationdistilled water (0.25 ml)
  3. customsealed
  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, 1:1, Rf 0.1)

Sources & evidence

ORD record
ord-834b7d937dc247de8fff4e1f07da25eb
Source dataset
uspto-grants-2015_12
Patent number
US09216992B2

Reaction notes

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