Sodium Hydroxide → HCID 15337394, compound

HRID 2269570Notes

Reaction equation

HRID 2269570 reaction equation
Br[C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[C:21]1(OB(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:20][S:17]([C:14]1[CH:15]=[CH:16][C:11]([C:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[S:6][C:2]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:12][CH:13]=1)(=[O:19])=[O:18]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 78412Phenyl dihydrogen orthoborateHCID 516892Sodium BicarbonateHCID 15337393HCID 15337393, compound

Product 1

HCID 15337394HCID 15337394, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-3-(4-(methanesulfonyl)phenyl) benzo-[b]thiophene (400 mg) from Step 3, phenylboric acid (590 mg), Pd (PPh3)4 (89 mg) and 1 molar NaOH in toluene (6 mL) and EtOH (8 mL) was refluxed for 24 hrs. After cooling to 25° C. a saturated NaHCO3 solution was added and the mixture was extracted with Et2O (2×), the organic portions were combined, washed with brine, dried over MgSO4, filtered and the solvent evaporated under vacuum. Purification by column chromatography using 2% isopropanol in hexane afforded the title compound. m.p. 172.9-173.9° C.

Workup

  1. temperaturewas refluxed for 24 hrs
  2. additionwas added
  3. extractionthe mixture was extracted with Et2O (2×)
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent evaporated under vacuum
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-56e403dbfff04b31b3118e9da8380584
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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