Sodium Dithionite → Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate

HRID 2209013Notes

Reaction equation

[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[C:4]([Cl:19])[N:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C1COCC1.O>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([Cl:19])=[CH:5][C:6]=1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

Tert-butyl 2,6-dichloro-3-nitropyridin-4-ylcarbamate 2.42 (2.0 g, 6.49 mmol) was dissolved in THF (10 mL) and cooled to 0° C. in ice-bath. To this solution sodium dithionite (3.39 g, 19.47 mmol), and NaHCO3 (1.6 g) dissolved in 10 mL of water, were added and the mixture was stirred at 0° C. After 1 hr, LC/MS indicated full conversion to desired product, solvent was removed under reduced pressure. Solids re-dissolved and extracted with ethyl acetate and water. Organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Residue obtained was recrystallized from acetonitrile to obtain tert-butyl 3-amino-2,6-dichloropyridin-4-ylcarbamate 2.43 that was used for next step without further purification.

Workup

additionwere added

Sources & evidence

ORD record: ord-2b0c0463740f49e0a59e6ceea482c8d2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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