Indane → HCID 67071193, compound

HRID 2357013Notes

Reaction equation

HRID 2357013 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([C@@H:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16](Br)[CH:17]=2)[CH2:12]1)[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([CH3:37])[CH3:36].[CH3:44][NH:45][SH:46](=[O:48])=[O:47].C1C2C(=CC=CC=2)CC1>FC(C1C=CC=CC=1)(F)F.[H-].[Na+]>[C:1]([O:5][C:6](=[O:21])[N:7]([C@@H:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N:45]([S:46]([C:41]3[CH:42]=[CH:43][C:38]([CH:35]([CH3:37])[CH3:36])=[CH:39][CH:40]=3)(=[O:48])=[O:47])[CH3:44])[CH:17]=2)[CH2:12]1)[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10326IndaneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 67071034HCID 67071034, compoundHCID 178438937HCID 178438937, compound

Product 1

HCID 67071193HCID 67071193, compoundYield 302.2%

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 7368(Trifluoromethyl)benzeneSolvent2×

Conditions

Temperature
150 °C

Procedure

0.68 mmol of ((S)-5-Bromo-indan-2-yl)-propyl-carbamic acid tert-butyl ester were dissolved in 2.5 ml of trifluoromethylbenzene. 0.077 mg of tris(dibenzylidenaceton)-dipalladium(0) (0.08 mmol) and 0.068 mg of tritert.butylphosphine (0.34 mmol) were added. 0.362 mg of 4-isopropyl-benzene-N-methyl-sulfonamide (1.7 mmol) dissolved in 2.5 ml of trifluoromethylbenzene were treated with 0.068 mg of sodium hydride (60% in mineral oil), and the resulting suspension added to the indane solution. The reaction mixture was stirred at 150° C. for 1 h in the microwave (CEM), the solvent evaporated under reduced pressure, water added and the aqueous phase extracted twice with diethyl ether. The combined organic layers were dried over magnesium sulfate, filtered, and the solvent evaporated to yield 1 g of a brownish oil that was further purified via silica gel chromatography using cyclohexane/ethyl acetate 7.5% as eluent. Fractions containing the product were combined and the solvent evaporated to yield 0.197 g of the product.

Workup

  1. customthe solvent evaporated under reduced pressure, water
  2. additionadded
  3. extractionthe aqueous phase extracted twice with diethyl ether
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-118551bcba16473e90ceadf02c4a2b17
Source dataset
uspto-grants-2010_07
Patent number
US07759397B2

Reaction notes

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