Sodium hydride → HCID 68912510, compound

HRID 870353Notes

Reaction equation

HRID 870353 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:19][CH:20]=[CH2:21])[C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH:36]([C:39]1[CH:44]=[CH:43][C:42]([S:45]([NH:48][CH3:49])(=[O:47])=[O:46])=[CH:41][CH:40]=1)([CH3:38])[CH3:37].[H-].[Na+]>FC(F)(F)C1C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:19][CH:20]=[CH2:21])[C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:48]([S:45]([C:42]3[CH:43]=[CH:44][C:39]([CH:36]([CH3:38])[CH3:37])=[CH:40][CH:41]=3)(=[O:46])=[O:47])[CH3:49])[CH:14]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 19684294HCID 19684294, compoundHCID 68913985HCID 68913985, compound

Product 1

HCID 68912510HCID 68912510, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7368(Trifluoromethyl)benzeneSolvent2×

Procedure

In an inert atmosphere (argon), allyl-((S)-6-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester (749 mg, 2.0 mmol) was dissolved in trifluortoluol (20 ml) at room temperature. Tris(dibenzylideneacetone)dipalladium (92 mg, 0.1 mmol) and tri-tert-butyl-phosphane (61 mg, 0.3 mmol) were added to the reaction mixture. In a separate flask, 4-Isopropyl-N-methyl-benzenesulfonamide (427 mg, 2 mmol) was dissolved in trifluortoluol (20 ml) at 65° C. Sodium hydride (50% in oil) (96 mg, 2 mmol) was added, stirred for 5 minutes and added to the reaction mixture. The reaction mixture was dispensed into 3 vials and stirred for 1 hour at 150° C. in the microwave (CEM). The combined reaction mixture was evaporated to dryness. H20 (50 ml) was added and extracted three times with 50 ml diethylether. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield crude product (1.12 g, 68%).

Workup

  1. additionadded to the reaction mixture
  2. stirringstirred for 1 hour at 150° C. in the microwave (CEM)
  3. customThe combined reaction mixture
  4. customwas evaporated to dryness
  5. additionH20 (50 ml) was added
  6. extractionextracted three times with 50 ml diethylether
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-f56432af24bf4798982d657551c7197b
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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