Sodium Carbonate → HCID 57585107, compound

HRID 2077568Notes

Reaction equation

HRID 2077568 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]2[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10][C:8]=2[N:9]=1)(=[O:3])[CH3:2].Br[C:18]1[CH:19]=[C:20]([O:24][CH2:25][CH2:26][N:27]2[CH2:31][CH2:30][CH2:29][C:28]2=[O:32])[CH:21]=[N:22][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].O1CCOCC1>[O:32]=[C:28]1[CH2:29][CH2:30][CH2:31][N:27]1[CH2:26][CH2:25][O:24][C:20]1[CH:19]=[C:18]([C:12]2[CH:11]=[CH:10][C:8]3[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][C:7]=3[CH:13]=2)[CH:23]=[N:22][CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 670970361-[2-[(5-Bromo-3-pyridinyl)oxy]ethyl]-2-pyrrolidinoneHCID 86627998HCID 86627998, compound

Product 1

HCID 57585107HCID 57585107, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a 5 ml CEM microwave tube was added 2-acetamidobenzo[d]thiazol-6-ylboronic acid (0.1 g, 0.4 mmol), 1-(2-(5-bromopyridin-3-yloxy)ethyl)pyrrolidin-2-one (0.2 g, 0.6 mmol), sodium carbonate (0.6 ml, 1 mmol), Pd FibreCat® (Anchored homogeneous catalyst, Johnson Matthey, West Deptford, N.J. (30% wt, 45 mg), and dioxane (3 mL). The vial was sealed and placed into CEM microwave for 20 min. at 100° C., with 100 watts of power via Powermax®. The reaction mixture was partitioned between EtOAc/water. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with water, brine, dried over MgSO4 and removed solvent. The crude product was purified using SiO2 chromatography with DCM:MeOH (95%:5%) solvent system to afford the product as white solid. Wt: 45.0 mg. MS (ESI pos. ion) m/z: 397.3. Calc'd exact mass for C20H20N4O3S: 396.46. 1H NMR (300 MHz, chloroform-d) δ ppm 1.99-2.14 (m, 2H) 2.33 (s, 3H) 2.42 (t, J=8.11 Hz, 2H) 3.62 (t, J=7.09 Hz, 2H) 3.74 (t, J=5.19 Hz, 2H) 4.25 (t, J=5.19 Hz, 2H) 7.43 (d, J=2.48 Hz, 1H) 7.62 (dd, J=8.48, 1.90 Hz, 1H) 7.81 (d, J=8.33 Hz, 1H) 7.99 (d, J=1.46 Hz, 1H) 8.27 (d, J=2.63 Hz, 1H) 8.50 (s, 1H).

Workup

  1. customThe vial was sealed
  2. customThe reaction mixture was partitioned between EtOAc/water
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over MgSO4
  6. customremoved solvent
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-55f1d06bf76c4d619e66de6fac36f28b
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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