3-Fluoro-4-((3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy)aniline → HCID 178507759, compound

HRID 2241419Notes

Reaction equation

COC1C=CC(C[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:25])=[C:11]3[C:10]([I:26])=[N:9]2)=CC=1>C(O)(C(F)(F)F)=O>[F:25][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:8][N:9]=[C:10]([I:26])[C:11]=12)[NH2:24]

Participants

Conditions

Temperature: 50 °C

Procedure

Dissolved 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (50 mg, 0.102 mmol; prepared as in Example 7, Step B) in excess TFA (1 mL). The dark solution was stirred at 50° C. for (20 hours. The mixture was concentrated in vacuo, using toluene (2×5 mL) to azeotrope residual TFA. The crude was partitioned between CH2Cl2 and NaHCO3. The cloudy organic layer was evaporated and the resulting semi-solid triturated with diethyl ether to afford the desired product. Yield: 33 mg, 87%. LRMS (APCI pos) m/e 371.1 (M+H).

Workup

concentrationThe mixture was concentrated in vacuo
customThe crude was partitioned between CH2Cl2 and NaHCO3
customThe cloudy organic layer was evaporated
customthe resulting semi-solid triturated with diethyl ether

Sources & evidence

ORD record: ord-a3f6632e6a384915a329a5b25e792bae
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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