Dimethylamine → HCID 67266801, compound

HRID 602791Notes

Reaction equation

HRID 602791 reaction equation
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[C:22]([O:26][C:27]([N:29]1[C:41]2[CH2:40][CH:39]([C:42]([S:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)(=[O:50])=[O:49])([C:44]([O:46][CH3:47])=[O:45])[CH3:43])[CH2:38][CH2:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[C:33](Br)[CH:34]=2)=[O:28])([CH3:25])([CH3:24])[CH3:23].[CH3:58][NH:59][CH3:60].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:22]([O:26][C:27]([N:29]1[C:41]2[CH2:40][CH:39]([C:42]([S:48]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)(=[O:50])=[O:49])([C:44]([O:46][CH3:47])=[O:45])[CH3:43])[CH2:38][CH2:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[C:33]([N:59]([CH3:60])[CH3:58])[CH:34]=2)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

9

Reactant 4

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 67267564HCID 67267564, compound

Product 1

HCID 67266801HCID 67266801, compoundYield 24.2%

Reagents, catalysts & solvents 4

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Under argon a flask was charged with 24 mg of (0.03 mmol, 0.05 eq) tris(dibenzylidene-acetone) dipalladium, 16 mg (0.05 mmol, 0.1 eq) of 2(di-tertbutylphosphino)biphenyl and 85 mg (0.88 mmol, 1.7 eq) of sodium tert-butylate, evacuated and backfilled with argon. 300 mg (0.52 mmol) of (RS,SR)-2-(-1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-6-bromo-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester in 15 ml of toluene were added, followed by a solution of 1.95 ml 2M (3.9 mmol, 7.5 eq) of dimethylamine in THF. The solution was heated to 80° C. overnight in a sealed tube. The mixture was diluted with EtOAc and a saturated solution of Na2CO3 was added. The inorganic layer was extracted with EtOAc. The combined organic phases were washed with brine and dried over Na2SO4. Column chromatography yielded 68 mg (24%) of (RS,SR)-2-(-1-benzenesulfonyl-1-methoxycarbonyl-ethyl)-6-dimethylamino-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester as orange oil, MS: 541 (MH+).

Workup

  1. customevacuated
  2. extractionThe inorganic layer was extracted with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-28f248a397ea437f962146d5c54c34ae
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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