Ethanol → 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-2-chloro-5-fluorobenzenamine

HRID 2241385Notes

Reaction equation

HRID 2241385 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][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]=[C:22]([Cl:24])[C:21]([N+:25]([O-])=O)=[CH:20][C:19]=4[F:28])=[C:11]3[C:10]([I:29])=[N:9]2)=[CH:5][CH:4]=1.CCO>CCOC(C)=O>[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[C:19]([F:28])=[CH:20][C:21]([NH2:25])=[C:22]([Cl:24])[CH:23]=4)=[C:11]3[C:10]([I:29])=[N:9]2)=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 685164081-(4-methoxybenzyl)-4-(5-chloro-2-fluoro-4-nitrophenoxy)-3-iodo-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 685133884-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-2-chloro-5-fluorobenzenamineYield 74.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(4-methoxybenzyl)-4-(5-chloro-2-fluoro-4-nitrophenoxy)-3-iodo-1H-pyrazolo[3,4-b]pyridine (2.85 g, 5.14 mmol), SnCl2 dihydrate (4.64 g, 20.6 mmol) and EtOH (70 mL) was heated to 70° C. for 8 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc, washed with saturated aqueous Na2CO3, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (5% MeOH in CH2Cl2) to afford the product (2.02 g, 64% yield) as a light yellow solid. LRMS (APCI pos) m/e 524.9 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with saturated aqueous Na2CO3
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c1e8eec9dbdb4180b881c83366e59312
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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