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

HRID 2241199Notes

Reaction equation

HRID 2241199 reaction equation
[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][CH:19]=4)=[C:11]3[C:10]([CH3:27])=[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][CH:19]=4)=[C:11]3[C:10]([CH3:27])=[N:9]2)=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25517Ammonium ChlorideHCID 685162851-(4-methoxybenzyl)-3-methyl-4-(4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 685150574-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)anilineYield 93.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL round-bottomed flask with stir bar containing 1-(4-methoxybenzyl)-3-methyl-4-(4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine (0.185 g, 0.474 mmol) was added MeOH (10 mL) and THF (10 mL) followed by zinc (0.155 g, 2.37 mmol). Next, saturated NH4Cl (0.5 mL) was added with stirring. Concentrated HCl (0.5 mL) was added until all solids dissolved (except for some zinc powder) and the pH had dropped to 2. The reaction was stirred for 18 hours at room temperature. The reaction was concentrated and partitioned between EtOAc (100 mL) and 1:1 saturated NaHCO3/water (100 mL). The aqueous phase washed with EtOAc (75 mL). The combined organic phases were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The product (160 mg, 82%) was obtained as a yellow gum. LRMS (esi pos) m/e 361 (M+1).

Workup

  1. stirringwith stirring
  2. additionhad dropped to 2
  3. stirringThe reaction was stirred for 18 hours at room temperature
  4. concentrationThe reaction was concentrated
  5. custompartitioned between EtOAc (100 mL) and 1:1 saturated NaHCO3/water (100 mL)
  6. washThe aqueous phase washed with EtOAc (75 mL)
  7. washThe combined organic phases were washed with brine (50 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-826b75a604b04292ba3ab2848b7b2e21
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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