5-Amino-2-naphthol → 6-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)naphthalen-1-amine

HRID 2115868Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([OH:12])=[CH:7]2.[H-].[Na+].I[C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[NH:22][N:23]=[CH:24][C:17]=12>CN(C=O)C>[NH:22]1[C:18]2=[N:19][CH:20]=[CH:21][C:16]([O:12][C:6]3[CH:7]=[C:8]4[C:3](=[CH:4][CH:5]=3)[C:2]([NH2:1])=[CH:11][CH:10]=[CH:9]4)=[C:17]2[CH:24]=[N:23]1

Participants

Conditions

Temperature: 0 °C

Procedure

5-Aminonaphthalen-2-ol (356 mg, 2.24 mmol) was dissolved in DMF (2.5 mL) then cooled to 0° C. Sodium hydride (94 mg) was added slowly and the stirring was continued for 15 min at 0° C. 4-Iodo-1H-pyrazolo[3,4-b]pyridine (274 mg, 1.12 mmol) was then added slowly and the reaction was heated at 100° C. for 16 h, followed by 4.5 h at 120° C. The mixture was partitioned between water and EtOAc then washed with water, 1N aqueous NaOH, and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo to give 6-(1H-pyrazolo[3,4-b]pyridin-4-yloxy)naphthalen-1-amine as a brown solid. MS (ESI, pos. ion) m/z: 277.1 (M+1).

Workup

temperaturethe reaction was heated at 100° C. for 16 h
waitfollowed by 4.5 h at 120° C
customThe mixture was partitioned between water and EtOAc
washthen washed with water, 1N aqueous NaOH, and brine
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f361a2d81c2242cfb85138c49a611972
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435823B2

Reaction notes

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