Potassium Phosphate, Tribasic → (4-isopropyl-piperazin-1-yl)-(3-methyl-2-o-tolyl-3H-imidazol-4-yl)-methanone

HRID 12449

반응식

HRID 12449 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:9]1([CH3:18])[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O.Cl[C:20]1[N:24]([CH3:25])[C:23]([C:26]([N:28]2[CH2:33][CH2:32][N:31]([CH:34]([CH3:36])[CH3:35])[CH2:30][CH2:29]2)=[O:27])=[CH:22][N:21]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH:34]([N:31]1[CH2:32][CH2:33][N:28]([C:26]([C:23]2[N:24]([CH3:25])[C:20]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[CH3:18])=[N:21][CH:22]=2)=[O:27])[CH2:29][CH2:30]1)([CH3:36])[CH3:35]

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 27332672-Methylphenyl boronic acidHCID 59338485(2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone

생성물 1

HCID 59337779(4-isopropyl-piperazin-1-yl)-(3-methyl-2-o-tolyl-3H-imidazol-4-yl)-methanone

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A reaction vessel is charged with Pd2(dba)3 (0.0183 g, 0.02 mmol), P(t-Bu)3HBF4 (0.0116 g, 0.04 mmol), K3PO4 (0.127 g, 0.60 mmol), o-tolylboronic acid (0.0408 g, 0.30 mmol) and (2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone (0.0542 g, 0.20 mmol). Toluene (2.4 mL, anhydrous) is added and the reactor is flushed and sealed under argon. The reaction is stirred at 100° C. for 16 hr; then at rt water (2 mL) and isopropyl acetate (1 mL) are added. The organic layer is removed and the aqueous layer is reextracted with isopropyl acetate. The combined organic extracts are passed through a plug of celite with EtOAc as the eluent. The filtered solution is concentrated to ˜⅓ volume in vacuo and the resulting solution is purified via SCX solid phase extraction. Purification of this crude product via preparative LC-MS gives (4-isopropyl-piperazin-1-yl)-(3-methyl-2-o-tolyl-3H-imidazol-4-yl)-methanone. LC-MS (M+1) 327.3.

후처리

  1. customthe reactor is flushed
  2. customsealed under argon
  3. additionthen at rt water (2 mL) and isopropyl acetate (1 mL) are added
  4. customThe organic layer is removed
  5. concentrationThe filtered solution is concentrated
  6. customthe resulting solution is purified via SCX solid phase extraction
  7. customPurification of this crude product via preparative LC-MS

출처 및 근거

ORD 기록
ord-a881f7fabe29446d94622d478d282695
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728009B1

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