Water → 6-Chloro-3-(4-methoxybenzyl)imidazo[1,2-b]pyridazine

HRID 69158노트

반응식

HRID 69158 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=O)=[CH:9][N:10]=2)[N:7]=1.[BH4-].[Na+].O.C([SiH](CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:11][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)=[CH:9][N:10]=2)[N:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 12052TriethylsilaneHCID 4311764Sodium borohydrideHCID 86635113(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(4-methoxy-phenyl)-methanone

생성물 1

HCID 866351126-Chloro-3-(4-methoxybenzyl)imidazo[1,2-b]pyridazine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

The compound (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-(4-methoxy-phenyl)-methanone (Stage 3.2, 2.04 g, 7.1 mmol) was suspended in ethanol (20 mL) with sodium borohydride (140 mg, 3.6 mmol) and stirred at rt for 7 h. Then water was added and the precipitate formed was filtered off. The yellow solid obtained was dried and then dissolved in TFA (50 mL). Triethylsilane (2.85 mL, 17.7 mmol) was added to the solution and it was stirred at rt for 30 min. the RM was poured into ice water. It was extracted with EtOAc and washed with aqueous 1 N sodium hydroxide solution then with brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by chromatography with DCM and MeOH. The title compound was obtained As a white solid (tR 1.1 min (conditions 2), MH+=274).

후처리

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. customThe yellow solid obtained
  4. customwas dried
  5. dissolutiondissolved in TFA (50 mL)
  6. stirringwas stirred at rt for 30 min. the RM
  7. extractionIt was extracted with EtOAc
  8. washwashed with aqueous 1 N sodium hydroxide solution
  9. dry with materialThe organic layer was dried over Na2SO4
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography with DCM and MeOH

출처 및 근거

ORD 기록
ord-f6b0ee18cfaf486195c4972917d2abe5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822468B2

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