7-Iodo-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine → 7-(5-methoxy-1-methyl-1H-indazol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine

HRID 1628025Notes

Reaction equation

I[C:2]1[N:14]([S:15]([C:18]2[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:5]2=[N:6][CH:7]=[C:8]3[CH:12]=[N:11][N:10]([CH3:13])[C:9]3=[C:4]2[CH:3]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH3:36])[N:31]=[C:30]2[Sn](C)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH3:36])[N:31]=[C:30]2[C:2]1[N:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:22])=[CH:23][CH:24]=2)(=[O:16])=[O:17])[C:5]2=[N:6][CH:7]=[C:8]3[CH:12]=[N:11][N:10]([CH3:13])[C:9]3=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a flask was added 7-iodo-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.090 g, 0.20 mmol, Preparation #1), Pd(Ph3P)4 (0.018 g, 0.016 mmol) and 5-methoxy-1-methyl-3-(trimethylstannyl)-1H-indazole (0.071 g, 0.22 mmol) in DMF (3 mL) and the mixture was heated to about 80° C. for about 17 h. The mixture was cooled to rt and then loaded directly on 12 g silica column and eluted with 0 to 100% EtOAc/DCM to provide 7-(5-methoxy-1-methyl-1H-indazol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.045 g, 47%): LC/MS (Table 2, Method c) Rt=1.47 min; MS m/z 487 (M+H)+.

Workup

temperatureThe mixture was cooled to rt
washeluted with 0 to 100% EtOAc/DCM

Sources & evidence

ORD record: ord-24e9a733ba45433dab05ad2d03bbcac1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785639B2

Reaction notes

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