Toluene → HCID 25232518, compound

Temperature

90 °C

In a typical run, 2-amino-5-bromothiazole monohydrobromide (Aldrich, 5.00 g, 0.0192 mol) was mixed with 40 mL of toluene, 40 mL of ethanol, and 20 mL of water. 2-Nitrophenyl boronic acid (3.2 g, 0.0192 mol) was added, along with 2.35 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) complex with CH2Cl2 (1:1) and 6.10 g of anhydrous sodium carbonate. The reaction mixture was stirred at 90° C. for 18 hours. It was then cooled to room temperature and concentrated. The resulting residue was mixed with 500 mL of EtOAc and washed with water (3×50 mL). The organic layer was filtered to remove the black precipitate. The filtrate was extracted with dilute 1N HCl. The combined aqueous layers were concentrated to near dryness. The resulting residue was purified by preparative HPLC using a mixture of aqueous acetonitrile that has been buffered with 0.1% TFA to afford 108 mg of 5-(2-nitro-phenyl)-thiazol-2-ylamine (MS, M++H=222).

1. temperatureIt was then cooled to room temperature
2. concentrationconcentrated
3. additionThe resulting residue was mixed with 500 mL of EtOAc
4. washwashed with water (3×50 mL)
5. filtrationThe organic layer was filtered
6. customto remove the black precipitate
7. extractionThe filtrate was extracted
8. additionwith dilute 1N HCl
9. concentrationThe combined aqueous layers were concentrated
10. customThe resulting residue was purified by preparative HPLC
11. additiona mixture of aqueous acetonitrile that

ORD record

ord-186606d734164cdf8af4fbb14fb02eb6

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093401B2