Potassium Phosphate, Tribasic → HCID 66688052, compound

HRID 2201019Notes

Reaction equation

HRID 2201019 reaction equation
Cl[C:2]1[N:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O>[C:15]1([C:2]2[N:14]=[CH:13][C:5]3[S:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:4]=3[CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86663081HCID 86663081, compound

Product 1

HCID 66688052HCID 66688052, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-chloro-3-azadibenzothiophene (1.3 g, 5.7 mmol), phenylboronic acid (0.87 g, 7.1 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (S-Phos) (0.09 g, 0.23 mmol), and potassium phosphate (3.3 g, 14.3 mmol) were mixed in 60 mL of toluene and 6 mL of water. Nitrogen is bubbled directly into the mixture for 30 minutes. Next, Pd2(dba)3 was added (0.05 g, 0.05 mmol) and the mixture was heated to reflux under nitrogen for 3 days. The mixture was cooled and the organic layer was separated. The organic layers are washed with brine, dried over magnesium sulfate, filtered, and evaporated to a residue. The residue was purified by column chromatography eluting with 5% ethyl acetate/hexanes. 0.4 g of desired product was obtained after purification.

Workup

  1. customNitrogen is bubbled directly into the mixture for 30 minutes
  2. additionNext, Pd2(dba)3 was added (0.05 g, 0.05 mmol)
  3. temperaturethe mixture was heated
  4. temperatureto reflux under nitrogen for 3 days
  5. temperatureThe mixture was cooled
  6. customthe organic layer was separated
  7. washThe organic layers are washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated to a residue
  11. customThe residue was purified by column chromatography
  12. washeluting with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-49cd346414ed45b29fdfefeca163e221
Source dataset
uspto-grants-2016_06
Patent number
US09359549B2

Reaction notes

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