Water → HCID 86762476, compound

HRID 404895Notes

Reaction equation

HRID 404895 reaction equation
[C:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[C:17]1[S:18][CH:19]=[CH:20][N:21]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[O:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 86762476HCID 86762476, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

N-Boc-4-hydroxy-aniline (3.9 g, 0.019 mol) was combined with 2-bromothiazole (2.4 mL, 0.027 mol) in DMSO (20 mL) at room temperature. K2CO3 (3.9 g, 0.028 mol) was added and with rapid stirring, the reaction mixture was heated at about 140° C. for 5 hours. After cooling to room temperature, the reaction mixture was poured into water (300 mL), extracted with ethyl acetate (2×) and the combined organics were dried over MgSO4. Decolorizing charcoal was added, stirred for 30 minutes and filtered through a plug of celite and silica (1:1) to obtain an amber filtrate. The solvent was removed by rotary evaporation and the residue was purified by flash column chromatography (ethyl acetate:hexanes; 5%-50% ethyl acetate gradient) to give the title compound (1.4 g, 4.8 mmol, 25%) MS (ESI APCI) m/z 293.0 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ 9.49 (s, 1H) 7.53 (d, J=9.0 Hz, 2H) 7.21-7.28 (m, 2H) 7.16-7.19 (m, 2H) 1.48 (s, 9H).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialthe combined organics were dried over MgSO4
  4. additionDecolorizing charcoal was added
  5. filtrationfiltered through a plug of celite and silica (1:1)
  6. customto obtain an amber filtrate
  7. customThe solvent was removed by rotary evaporation
  8. customthe residue was purified by flash column chromatography (ethyl acetate:hexanes; 5%-50% ethyl acetate gradient)

Sources & evidence

ORD record
ord-2ffca9df988e405f9d7a68358de49af1
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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