Ammonium Chloride → HCID 86689253, compound

HRID 1409515Notes

Reaction equation

HRID 1409515 reaction equation
[Li]CCCC.Br[C:7]1[C:8]([C:13]#[N:14])=[N:9][CH:10]=[CH:11][CH:12]=1.[Br:15][C:16]1[CH:17]=[C:18]2[C:29](=[CH:30][CH:31]=1)[O:28][C:21]1[C:22]([F:27])=[N:23][C:24]([Cl:26])=[CH:25][C:20]=1[C:19]2=[N:32]S(C(C)(C)C)=O.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Br:15][C:16]1[CH:17]=[C:18]2[C:19]3([C:7]4[C:8](=[N:9][CH:10]=[CH:11][CH:12]=4)[C:13]([NH2:14])=[N:32]3)[C:20]3[CH:25]=[C:24]([Cl:26])[N:23]=[C:22]([F:27])[C:21]=3[O:28][C:29]2=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 8176943-Bromopyridine-2-carbonitrileHCID 86658361N-(7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamideHCID 178418339Butyllithium

Product 1

HCID 86689253HCID 86689253, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of n-BuLi (1.6 M in hexane; 0.174 ml, 0.278 mmol, Aldrich) was added dropwise to a solution of 3-bromopicolinonitrile (50.9 mg, 0.278 mmol, Alfa Aesar) in THF (5 ml) at −95° C. After 2 min a solution of N-(7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide (100 mg, 0.232 mmol, example x) in THF (3 mL) was added. After 5 min aqueous, saturated NH4Cl solution was added and the reaction mixture was allowed to warm to rt. EtOAc was added, the organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel (20-100% EtOAc/hexanes). The title compound was obtained as a yellow solid (38 mg, 0.088 mmol). MS m/z=432.8 [M+H]+. Calculated for C18H9BrClFN4O: 431.65.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (20-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0ff666dcd2604db392de19a219bf966a
Source dataset
uspto-grants-2014_12
Patent number
US08921363B2

Reaction notes

Loading…