Potassium Acetate → 1111638-14-2

HRID 500732Notes

Reaction equation

HRID 500732 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:5]2=[N:6][CH:7]=1.[B:18]1(B2OC(C)(C)C(C)(C)O2)[O:22]C(C)(C)C(C)(C)[O:19]1.C([O-])(=O)C.[K+]>CN(C=O)C>[C:14]([O:13][C:11]([N:8]1[C:5]2=[N:6][CH:7]=[C:2]([B:18]([OH:22])[OH:19])[CH:3]=[C:4]2[CH2:10][CH2:9]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 57856243HCID 57856243, compound

Product 1

HCID 578562361111638-14-2

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of tert-butyl 5-bromo-2,3-dihydropyrrolo[2,3-b]pyridine-1-carboxylate (B-12-2) (725 mg, 2.42 mMoles) and bis(pinacolato) diboron (894 mg, 3.52 mMoles) in 20 ml DMF were added potassium acetate (691 mg, 7.04 mMoles) and [1,1-Bis(diphenylphosphino)-ferrocene]dichloropalladium (II) dichloromethane (1:1) complex (34.3 mg, 0.0469 mMoles). The mixture was heated in 100° C. microwave reactor for 60 min. LCMS indicated reaction was complete. RXN was filtered and the filtrate was concentrated to dryness under high vacuum. The residual was partitioned between EtOAc and saturated aqueous NaCl. The aqueous layer was extracted with EtOAc (3×40 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a 25 g silica gel cartridge with 1˜4% MeOH in DCM as solvent. The crude product and was used as is in the next step.

Workup

  1. customreaction
  2. filtrationRXN was filtered
  3. concentrationthe filtrate was concentrated to dryness under high vacuum
  4. customThe residual was partitioned between EtOAc and saturated aqueous NaCl
  5. extractionThe aqueous layer was extracted with EtOAc (3×40 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on a 25 g silica gel cartridge with 1˜4% MeOH in DCM as solvent

Sources & evidence

ORD record
ord-05f1a1ecbfac42ef83f423e7e5523255
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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