Potassium Phosphate, Tribasic → HCID 71768629, compound

HRID 1487054Notes

Reaction equation

HRID 1487054 reaction equation
Cl[C:2]1[CH:3]=[C:4]([S:16]([N:19]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[CH3:31])[CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:18])=[O:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH:32]1(B(O)O)[CH2:34][CH2:33]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:32]1([C:2]2[CH:3]=[C:4]([S:16]([N:19]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=3[CH3:31])[CH2:20][CH:21]([CH3:22])[CH3:23])(=[O:17])=[O:18])[CH:5]=[CH:6][C:7]=2[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:34][CH2:33]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 72190528HCID 72190528, compound

Product 1

HCID 71768629HCID 71768629, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 3-chloro-N-(2,4-dimethylphenyl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (100 mg, 0.215 mmol), cyclopropylboronic acid (46.1 mg, 0.536 mmol), tricyclohexylphosphine (12.03 mg, 0.043 mmol) and tripotassium phosphate (137 mg, 0.644 mmol) in toluene (4 mL) and water (0.2 mL), was added palladium(II) acetate (approximately 4.82 mg, 0.021 mmol) ensuring all particles were below solvent level. The reaction vessel was sealed and heated by microwaves (Emrys Optimiser) to 120° C. for 30 minutes. After cooling, the reaction mixture was passed through a pre-packed silica column (500 mg) to remove palladium residues, eluting with methanol. The reaction solution was evaporated in vacuo to and purified by mass directed autoprep (formic acid modifier). The appropriate fractions were concentrated under a stream of nitrogen to give the required product, 34 mg. LCMS [LCMS1] Rt 1.55 min, m/z (ES+) 472 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customto remove palladium residues
  4. washeluting with methanol
  5. customThe reaction solution was evaporated in vacuo to and
  6. custompurified by mass
  7. concentrationThe appropriate fractions were concentrated under a stream of nitrogen

Sources & evidence

ORD record
ord-8f4e119d802446efa969c1882d840e65
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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