Cesium carbonate → US9814704, Example 121

HRID 712556

반응식

HRID 712556 반응식
[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]

참가 물질

5

반응물 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

생성물 1

HCID 46235578US9814704, Example 121수율 51%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fd814e9f45084147b6655b089463595a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181247B2

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