Hexane → HCID 22401496, compound

HRID 260482Notes

Reaction equation

HRID 260482 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][NH:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([C:18]=1[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[CH:16][C:15]([Cl:28])=[CH:14][CH:13]=2)=[O:9].B(Br)(Br)Br.CCCCCC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][CH:31]=1)[CH2:6][NH:7][C:8]([C:10]1[NH:11][C:12]2[C:17]([C:18]=1[S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:21])=[CH:16][C:15]([Cl:28])=[CH:14][CH:13]=2)=[O:9]

Participants

6

Reactant 4

HCID 8058HexaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 22401528HCID 22401528, compound

Product 1

HCID 22401496HCID 22401496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a saturated solution of N-(3-methoxybenzyl) 3-phenylsulfonyl-5-chloroindole-2-carboxamide (1.37 g, 3.0 mmol) in dry methylene chloride (140 mL) under an inert atmosphere was added boron tribromide in hexane (1M, 10 mL, 10 mmol). After stirring for 12-20 hours, the reaction was neutralized by addition of aq. NaHCO3. After two hours, the solution was made weakly acidic by addition of dilute HC1. The precipitated product was collected by filtration and then the aqueous filtrate extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and the solvent evaporated. The residue was triturated with diethyl ether to give additional product. The solids were combined and crystallized from hot methanol/ethyl acetate to give analytically pure product, mp 73.5°-274.5° C.

Workup

  1. waitAfter two hours
  2. additionthe solution was made weakly acidic by addition of dilute HC1
  3. filtrationThe precipitated product was collected by filtration
  4. extractionthe aqueous filtrate extracted with ethyl acetate
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was triturated with diethyl ether
  9. customto give additional product
  10. customcrystallized from hot methanol/ethyl acetate
  11. customto give analytically pure product, mp 73.5°-274.5° C.

Sources & evidence

ORD record
ord-b873fcee4f414009827aa5ee6418b811
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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