Pyridine → HCID 67174946, compound

HRID 1256065Notes

Reaction equation

HRID 1256065 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:11](Cl)(=[O:13])=[O:12].[NH2:15][C:16]1[C:17]([F:26])=[CH:18][C:19]2[CH2:23][O:22][B:21]([OH:24])[C:20]=2[CH:25]=1.N1C=CC=CC=1>C(#N)C>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:11]([NH:15][C:16]1[C:17]([F:26])=[CH:18][C:19]2[CH2:23][O:22][B:21]([OH:24])[C:20]=2[CH:25]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24901388HCID 24901388, compoundHCID 457914292-fluoro-4-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 67174946HCID 67174946, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-fluoro-4-nitrobenzene-1-sulfonyl chloride (1.336 g, 5.57 mmol) and 6-amino-5-fluorobenzo[c][1,2]oxaborol-1(3H)-ol (0.93 g, 5.57 mmol) in 20 mL of ACN was added pyridine (900 uL, 11.14 mmol) dropwise. The reaction mixture was stirred at room temperature for 16 hours. After quenched with water, the solvent was removed in vacuo. The residue was extracted with ethyl acetate three times, and washed with water and brine. The organic layer was dried over Na2SO4, and concentrated to give 1.84 g of the title compound as a yellow residue. MS calcd for (C13H9BF2N2O6S): 370.0. MS found (ESI negative): (M−H)−=368.9

Workup

  1. customAfter quenched with water
  2. customthe solvent was removed in vacuo
  3. extractionThe residue was extracted with ethyl acetate three times
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf4455bd13754ee084cbe367d8d039b4
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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