Potassium Phosphate, Tribasic → HCID 70202778, compound

HRID 2367930Notes

Reaction equation

HRID 2367930 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.Br[C:21]1[S:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.Cl[Pd]Cl>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([C:21]3[S:22][CH:23]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[N:25]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2763213Methyl 2-bromothiazole-4-carboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 16218173{3-[(4-Methoxyphenyl)methoxy]phenyl}boronic acid

Product 1

HCID 70202778HCID 70202778, compound

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

3-(4-methoxybenzyloxy)phenylboronic acid (697 mg, 2.7 mmol, 1.5 eq.), methyl 2-bromothiazole-4-carboxylate (400 mg, 1.8 mmol, 1.0 eq.), dicyclohexyl (2′,6′-dimethoxybiphenyl-2-yl) phosphine (74 mg, 0.18 mmol, 10 mol %) and PdCl2 (20 mg, 0.090 mmol, 5 mol %) were dissolved in toluene (6 mL) and added to a solution of K3PO4 (828 mg, 3.6 mmol, 2.0 eq.) in water (0.6 mL). The reaction mixture was heated 20 min at 180° C. in a microwave reactor, allowed to cool, diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude 23 was used in the next step without purification.

Workup

  1. temperatureto cool
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude 23 was used in the next step without purification

Sources & evidence

ORD record
ord-401dcfef1b1f403f906802fef019ea7f
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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