Cesium carbonate → 7-iodo-2-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-2H-pyrazolo[4,3-b]pyridine

HRID 1522618Notes

Reaction equation

[I:1][C:2]1[C:3]2[C:4](=[CH:8][NH:9][N:10]=2)[N:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][O:17]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[I:1][C:2]1[C:3]2[C:4](=[CH:8][N:9]([CH2:12][CH2:13][CH2:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[N:10]=2)[N:5]=[CH:6][CH:7]=1.[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][CH2:14][O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C:3]=12

Participants

Conditions

Temperature: 120 °C

Procedure

7-Iodo-2H-pyrazolo[4,3-b]pyridine (200 mg, 0.816 mmol), 2-(3-bromopropoxy)tetrahydro-2H-pyran (182 mg, 0.816 mmol) and Cs2CO3 (532 mg, 1.633 mmol) were combined in DMF (5 mL) and the mixture was heated at 120° C. for 30 minutes in a microwave. The reaction mixture was then purified by preparative HPLC using a Sunfire Prep 5 μm C18, 75×30 mm column eluting with a gradient of 05-40% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) to give 7-iodo-2-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-2H-pyrazolo[4,3-b]pyridine and 7-iodo-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-pyrazolo[4,3-b]pyridine. MS [M+H] found 388.0.

Workup

customThe reaction mixture was then purified by preparative HPLC
washeluting with a gradient of 05-40% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA)

Sources & evidence

ORD record: ord-45182fbb8bbf40498aa76824e8c21957
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073918B2

Reaction notes

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