1,2-Dimethoxyethane → 2-[[4-(4-Chlorophenyl)-1-piperazinyl]methyl]-6-phenylimidazo[1,2-a]pyridine

HRID 1416299노트

반응식

HRID 1416299 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[N:10]=2)[CH:7]=1.C(COC)OC.[C:31]1(OB(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)(O)[O-].[Na+]>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:15]2[CH2:16][CH2:17][N:12]([CH2:11][C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:7][N:6]4[CH:8]=3)[CH2:13][CH2:14]2)=[CH:19][CH:20]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 78412Phenyl dihydrogen orthoborateHCID 516892Sodium BicarbonateHCID 193671286-Bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine

생성물 1

HCID 193671002-[[4-(4-Chlorophenyl)-1-piperazinyl]methyl]-6-phenylimidazo[1,2-a]pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

A mixture of 6-bromo-2-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]imidazo[1,2-a]pyridine. (Example 23; 0.091 g), tetrakis(triphenylphosphine)palladium (0) (Aldrich; 0.0078 g), and dimethoxyethane (2 mL) is stirred at room temperature for 10 min, at which time phenylboric acid (Aldrich; 0.0306 g) is added, followed by sodium bicarbonate (0.0565 g) in water (1 mL). The mixture is stirred at reflux for 3 h and then allowed to cool. Dimethoxyethane is removed under reduced pressure and the residue is partitioned between dichloromethane and aq. sodium bicarbonate. The organic layers are dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel using acetone/dichloromethane/methanol (50/200/1) to give 0.027 g of the title compound. MS m/z 402; 1H NMR (CDCl3) δ2.76, 3.21, 3.80, 6.84, 7.19, 7.37-7.58, 7.61, 7.64, 8.26.

후처리

  1. additionis added
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. customDimethoxyethane is removed under reduced pressure
  5. customthe residue is partitioned between dichloromethane and aq. sodium bicarbonate
  6. dry with materialThe organic layers are dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-d0483329bd6a45cc8e10050c02567012
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912246

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