2-Bromopropane → 3-[4-(Benzyloxy)phenyl]-6-fluoro-1-(1-methylethyl)-1H-pyrazolo[4,3-b]pyridine

HRID 573353Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][C:20]([F:24])=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:26][NH2:27].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH:35]([CH3:37])[CH3:36]>CC(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:17]3=[N:18][CH:19]=[C:20]([F:24])[CH:21]=[C:22]3[N:27]([CH:35]([CH3:37])[CH3:36])[N:26]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of [4-(benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone (100 mg) and hydrazine hydrate (77 mg) in 2-propanol (5 mL) was stirred at room temperature for 30 min and at 90° C. for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was dissolved in DMF (5 mL), and then Cs2CO3 (150 mg, 0.46 mmol) and 2-bromopropane (50.5 mg) were added successively. The mixture was stirred for 12 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (70.0 mg).

Workup

extractionextracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in DMF (5 mL)
stirringThe mixture was stirred for 12 h
extractionextracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record: ord-06fe055b39794ab5aaf1dbe4da08b2ec
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Reaction notes

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