Sodium Carbonate → HCID 68293844, compound

HRID 1472774Notes

Reaction equation

HRID 1472774 reaction equation
Br[C:2]1[N:3]=[CH:4][S:5][C:6]=1Br.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[C:11]([CH3:18])[CH:10]=1.O1[CH2:24][CH2:23]OCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[N:3]=[CH:4][S:5][C:6]=2[C:12]2[CH:11]=[CH:10][C:9]([Cl:8])=[CH:14][C:23]=2[CH3:24])=[C:11]([CH3:18])[CH:10]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 581297824,5-Dibromo-1,3-thiazole

Product 1

HCID 68293844HCID 68293844, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A round-bottomed flask was charged with 4,5-dibromothiazole (160 mg, 0.66 mmol), 4-chloro-2-methylphenylboronic acid (269 mg, 1.58 mmol) and Pd(PPh3)4 (38.1 mg, 0.033 mmol). After degassed, dioxane (5 mL) and aqueous sodium carbonate (3 mL, 2M, 6 mmol) was added. The reaction mixture was heated to 90° C. The progress of the reaction was monitored by TLC. After the reaction was complete, 50 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography to afford 170 mg of product as clear oil.

Workup

  1. customAfter degassed
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a814ce2dc28e45f282eefa8424b7b429
Source dataset
uspto-grants-2015_04
Patent number
US09012655B2

Reaction notes

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