Cesium carbonate → HCID 86690881, compound

HRID 1465579Notes

Reaction equation

HRID 1465579 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[S:12][CH:13]=2)=[C:4]([CH3:23])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:31]1[CH:32]=[CH:33][C:34]([NH:37][CH2:38][CH2:39][O:40][CH3:41])=[N:35][CH:36]=1>CN(C=O)C>[CH3:41][O:40][CH2:39][CH2:38][NH:37][C:34]1[N:35]=[CH:36][C:31]([O:1][C:2]2[CH:3]=[C:4]([CH3:23])[C:5]([C:9]3[N:10]=[C:11]([NH:14][C:15](=[O:22])[C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[S:12][CH:13]=3)=[C:6]([CH3:8])[CH:7]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 295663835-Bromo-N-(2-methoxyethyl)pyridin-2-amineHCID 86690827HCID 86690827, compound

Product 1

HCID 86690881HCID 86690881, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 5-3 (325 mg, 1.0 mmol) in DMF (15 mL) were added cesium carbonate (650 mg, 2.0 mmol, 2.0 equiv) and Cu (19.5 mg, 0.30 mmol, 0.3 equiv). The solution was stirred at 100-110° C. for 60 min and added with 5-bromo-N-(2-methoxyethyl)pyridin-2-amine (29-2, 347 mg). The reaction mixture was stirred at 140° C. for 48 h. The reaction was quenched with water (40 mL) and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3) to give 29 (96 mg) in 16% yield: 1H NMR (500 MHz, CDCl3) δ 8.81 (d, 1 H), 7.72 (d, 1 H), 7.71 (d, 1H), 7.24 (m, 1 H), 6.81 (s, 1 H), 6.72 (d, 1 H), 6.49 (s, 1 H), 3.59 (t, 1 H), 3.51 (t, 1 H), 3.35 (s, 3 H), 2.01 (s, 6 H), ESI-MS=m/z 447.5 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at 140° C. for 48 h
  2. customThe reaction was quenched with water (40 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=3/1-1/3)

Sources & evidence

ORD record
ord-da6435840b204197b6df4ee85d1a4dbc
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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