Stannous chloride dihydrate → 2-chloro-4-(3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-5-methylaniline

HRID 2241282Notes

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[CH3:28])=[C:11]3[C:10]([I:29])=[N:9]2)=[CH:5][CH:4]=1.O.O.[Sn](Cl)Cl>C(O)C>[Cl:24][C:22]1[CH:23]=[C:18]([O:17][C:16]2[CH:15]=[CH:14][N:13]=[C:12]3[N:8]([CH2:7][C:6]4[CH:30]=[CH:31][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:9]=[C:10]([I:29])[C:11]=23)[C:19]([CH3:28])=[CH:20][C:21]=1[NH2:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 100 mL round bottom flask added 1-(4-methoxybenzyl)-4-(5-chloro-2-methyl-4-nitrophenoxy)-3-iodo-1H-pyrazolo[3,4-b]pyridine (544 mg, 0.99 mmol) and suspended in absolute ethanol (10 mL). Added tin(II)chloride dihydrate (1.1 g, 4.94 mmol) and stirred at 25° C. under N2(g) for 18 hours, during which a white precipitate formed. The reaction mixture was cooled to 0° C. and the solid was removed by filtration and washed with cold ethanol. The solid was air-dried to afford the desired product as white solid. Yield: 417 mg, 81%. LRMS (APCI pos) m/e 521.1 (M+H).

Workup

customformed
customthe solid was removed by filtration
washwashed with cold ethanol
customThe solid was air-dried

Sources & evidence

ORD record: ord-8c00ec82bbf04bccb8a339e60e91222b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723330B2

Reaction notes

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