Potassium Carbonate → tert-Butyl 2-(3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)phenoxy)acetate

HRID 910965Notes

Reaction equation

HRID 910965 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[N:9]=[C:10]([NH:13][C:14]2[CH:19]=[C:18]([S:20][C:21]3[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=3)[CH:17]=[CH:16][N:15]=2)[S:11][CH:12]=1.Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CN(C=O)C.O>[CH3:7][C:8]1[N:9]=[C:10]([NH:13][C:14]2[CH:19]=[C:18]([S:20][C:21]3[CH:22]=[C:23]([CH:24]=[CH:25][CH:26]=3)[O:27][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH:17]=[CH:16][N:15]=2)[S:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 578989303-(2-(4-Methylthiazol-2-ylamino)pyridin-4-ylthio)phenol

Product 1

HCID 24826426tert-Butyl 2-(3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)phenoxy)acetateYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium carbonate (1.08 g, 7.82 mmol), 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-ylthio)phenol (0.274 g, 0.869 mmol), and tert-butyl 2-bromoacetate (0.169 g, 0.869 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature overnight, then diluted with water and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified using prepacked silica gel column chromatography with 15-20% ethyl acetate to afford the desired product (0.224 g, 58.8% yield) as light yellow solid. 1H NMR (CDCl3) δ 8.08 (d, 1H), 7.33 (t, 1H), 7.15 (m, 1H), 7.04 (t, 1H), 6.98 (m, 1H), 6.57 (dd, 1H), 6.49 (dd, 1H), 6.33 (d, 1H), 4.50 (s, 2H, 2.22 (d, 3H), 1.46 (s, 9H); Mass spectrum (esi) m/z=430 (100)(M+H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-3189a4eb91754b03a211f6874cb80d0c
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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