Potassium hydroxy sulfite → HCID 136413190, compound

HRID 1502380Notes

Reaction equation

HRID 1502380 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](B3OC(C)(C)C(C)(C)O3)=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[N:8]=[CH:9]2)=[CH:4][N:3]=1.[OH:28]OS([O-])=O.[K+]>CO.ClCCl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:28])=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[N:8]=[CH:9]2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86674956HCID 86674956, compound

Product 1

HCID 136413190HCID 136413190, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 7-chloro-3-(2-chlorophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-naphthyridine (60 mg, 0.1 mmol) and Oxone® (370 mg, 0.6 mmol) in wet methanol (0.6 mL) and dichloromethane (0.2 mL) was stirred at 35° C. for 3 hours. The cooled reaction mixture was diluted with dichloromethane (50 mL) and washed with 1.0M citric acid in water (20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford an orange/red residue that was used in the next step without further purification (50 mg, 100%).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with 1.0M citric acid in water (20 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford an orange/red residue that
  8. customwas used in the next step without further purification (50 mg, 100%)

Sources & evidence

ORD record
ord-5899cf61a6384827876cb07ab58848d8
Source dataset
uspto-grants-2015_12
Patent number
US09206175B2

Reaction notes

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