Ammonium Chloride → 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine

HRID 2409041Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[N:14]([S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=[CH:12][C:5]2=[N:6][C:7]=1[C:8](=[N:10]O)[CH3:9].[NH4+].[Cl-]>CO.CC(O)=O.[Zn]>[F:1][C:2]1[CH:3]=[C:4]2[N:14]([S:15]([C:18]3[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:13]=[CH:12][C:5]2=[N:6][C:7]=1[CH:8]([NH2:10])[CH3:9]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanone oxime (0.75 mg, 2.16 mmol), zinc powder (7.06 g, 108 mmol), and NH4Cl (2.31 g, 43.2 mmol) in MeOH (30 mL) and HOAc (6 mL) was heated at 60° C. for 2 h. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was suspended in ammonia solution (50 mL) and extracted with DCM (50 mL×3). The combined extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. The crude was purified by SiO2 chromatography eluting with DCM/MeOH/Et3N to afford 0.5 g (97.7%) of 1-(6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethanamine as a yellow solid. MS (ESI): m/z=334.3 [M+1]+.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate concentrated under reduced pressure
extractionextracted with DCM (50 mL×3)
dry with materialThe combined extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude was purified by SiO2 chromatography
washeluting with DCM/MeOH/Et3N

Sources & evidence

ORD record: ord-60936a9188f84cbb97ddfe8112192e60
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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