Potassium Carbonate → HCID 24826502, compound

HRID 910969Notes

Reaction equation

HRID 910969 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]([O: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>[CH3:7][C:8]1[N:9]=[C:10]([NH:13][C:14]2[CH:19]=[C:18]([O: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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 24826062HCID 24826062, compound

Product 1

HCID 24826502HCID 24826502, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium carbonate (3.00 g, 21.7 mmol), 3-(2-(4-methylthiazol-2-ylamino)pyridin-4-yloxy)phenol (0.750 g; 2.51 mmol), and tert-butyl 2-bromoacetate (0.489 g, 2.51 mmol) was stirred in DMF (20 mL) overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate was washed with water and brine, dried and concentrated. The residue was purified via MPLC (Biotage) eluting with 3:2 hexane:ethyl acetate to afford the desired product as a white powder. 1H NMR (d6-DMSO) δ 11.01 (s, 1H), 8.16 (d, 1H), 7.38 (t, 1H), 6.85 (d, 1H), 6.79 (d, 1H), 6.74 (s, 1M), 6.56 (s, 1H), 6.49-6.52 (m, 2H), 4.68 (s, 2H), 2.21 (s, 3H), 0.90 (s, 9H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washthe ethyl acetate was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (Biotage)
  6. washeluting with 3:2 hexane

Sources & evidence

ORD record
ord-f0c1767d678e4857ad0c1000fd78a8fb
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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