Hydrochloric Acid → 4-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine

HRID 2241181노트

반응식

HRID 2241181 반응식
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=4[F:27])=[C:11]3[CH:10]=[N:9]2)=[CH:5][CH:4]=1.CO.[NH4+].[Cl-].Cl>[Zn].C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=4[F:27])=[C:11]3[CH:10]=[N:9]2)=[CH:28][CH:29]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25517Ammonium ChlorideHCID 672207711-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 685158574-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 1-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine (0.560 g, 1.42 mmol) in a MeOH (20 mL) and THF (5 mL) co-solvent was added zinc (0.464 g, 7.10 mmol), followed by saturated aqueous NH4Cl (5 mL). Next 6N aqueous HCl (3-4 mL) was added until all solids dissolved and the pH was 1-2. The reaction was stirred at room temperature for 18 hours. The resulting mixture was partitioned between DCM (30 mL) and saturated aqueous NH4Cl (30 mL). The phases were separated, and the aqueous phase was re-extracted with DCM (20 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated in vacuo. The resulting waxy solid (504 mg, 72%) was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=5.5 Hz, 1H), 7.72 (s, 1H), 7.32 (d, J=8.6 Hz, 2H), 7.02 (m, 1H), 6.82 (d, J=9.0 Hz, 2H), 6.40-6.55 (m, 3H), 5.61 (s, 2H), 3.82 (br s, 2H), 3.75 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −129.0 (m).

후처리

  1. dissolutiondissolved
  2. customThe resulting mixture was partitioned between DCM (30 mL) and saturated aqueous NH4Cl (30 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was re-extracted with DCM (20 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting waxy solid (504 mg, 72%) was used in the next step without purification

출처 및 근거

ORD 기록
ord-98e2c7c7044a4253b0bd23398383b752
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723330B2

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