Cesium carbonate → US9814704, Example 121

HRID 85040

反応式

HRID 85040 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]3[CH2:21][C:20](=[O:22])[N:19](COCC[Si](C)(C)C)[C:16]3=[N:17][CH:18]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:38][CH2:39][CH2:40][CH2:41]I>CN(C=O)C>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]2[CH:14]=[C:15]3[C:21]4([CH2:41][CH2:40][CH2:39][CH2:38]4)[C:20](=[O:22])[NH:19][C:16]3=[N:17][CH:18]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 123371,4-DiiodobutaneHCID 667788935-(3,4,5-Trimethoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one

生成物 1

HCID 46235578US9814704, Example 121収率 51%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-(3,4,5-trimethoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-pyrrolo[2,3-b]pyridin-2(3H)-one (Compound BN, 43 mg, 0.10 mmol) in DMF (2 mL) was added cesium carbonate (0.17 g, 0.50 mmol) and 1,4-diiodobutane (13 μL, 0.10 mmol). The resulting solution was stirred for 4 hr at room temperature, after which it was partitioned between EtOAc and H2O. The organic layer was separated, dried over MgSO4, filtered, and concentrated in vacuo. The residue was dissolved in 6 N HCl (10 mL) and MeOH (5 mL), and the resulting mixture was stirred at room temperature overnight, after which it was partitioned between EtOAc and H2O. The organic layer was concentrated in vacuo, and the residue was dissolved in EtOH (2 mL). Potassium acetate (100 mg) was then added, and the reaction was stirred for 2 hr. The resulting solution was purified via preparatory HPLC to give the title compound (18 mg, 51%). 1H NMR (CDCl3, 300 MHz): δ 9.53 (s, 1H), 8.32 (d, J=2.1 Hz, 1H), 7.56 (s, 1H), 6.69 (s, 2H), 3.95 (s, 6H), 3.90 (s, 3H), 2.28 (m, 2H), 2.24 (m, 2H), 1.97 (m, 4H). HPLC retention time: 2.00 minutes; MS ESI (m/z): 355.4 (M+1)+, calc. 354.

後処理

  1. customafter which it was partitioned between EtOAc and H2O
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in 6 N HCl (10 mL)
  7. stirringMeOH (5 mL), and the resulting mixture was stirred at room temperature overnight
  8. customafter which it was partitioned between EtOAc and H2O
  9. concentrationThe organic layer was concentrated in vacuo
  10. dissolutionthe residue was dissolved in EtOH (2 mL)
  11. additionPotassium acetate (100 mg) was then added
  12. stirringthe reaction was stirred for 2 hr
  13. customThe resulting solution was purified via preparatory HPLC

出典と根拠

ORDレコード
ord-d35b15c0853248fe895479f64dfcb14e
出典データセット
uspto-grants-2014_09
特許番号
US08846909B2

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