Potassium Carbonate → HCID 66816405, compound

HRID 2367931Notes

Reaction equation

HRID 2367931 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:25]1[CH2:26][CH2:27][CH2:28][CH2:29][CH:24]1[O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][O:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][CH:10]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27869332-(5-Bromopentyloxy)tetrahydro-2H-pyranHCID 66815744HCID 66815744, compound

Product 1

HCID 66816405HCID 66816405, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 2-(3-hydroxyphenyl)thiazole-4-carboxylate (24), (223 mg, 0.95 mmol, 1 eq.) and 2-(5-bromopentyloxy)tetrahydro-2H-pyran (357 mg, 1.42 mmol, 1.5 eq) in DMF (3 mL) was added powdered potassium carbonate (392 mg, 2.84 mmol, 3.0 eq.) The mixture was stirred vigorously for 4 h at 70° C., then concentrated in vacuo. The residue was diluted with ethyl acetate, washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (ethyl acetate:hexanes gradient). Yield 250 mg (65%). TLC Rf=0.44 (ethyl acetate:hexanes 3:7), MS m/z 322 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with NaH2PO4 buffer (pH 5, 1M) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (ethyl acetate:hexanes gradient)

Sources & evidence

ORD record
ord-80401f89c56942d8bf2a76a204ac4b8c
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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