Sodium Carbonate → 3-cyclohexyl-N-[(dimethylamino)sulfonyl]-2-(2-formylphenyl)-1H-indole-6-carboxamide

HRID 1394872Notes

Reaction equation

HRID 1394872 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([NH:19][S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[O:18])[CH:5]=2.[Li+].[Cl-].[C:28]([O-:31])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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>[CH:11]1([C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:17]([NH:19][S:20]([N:23]([CH3:24])[CH3:25])(=[O:22])=[O:21])=[O:18])=[CH:7][CH:8]=3)[NH:3][C:2]=2[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[CH:28]=[O:31])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 587651502-bromo-3-cyclohexyl-N-(dimethylsulfamoyl)-1H-indole-6-carboxamide

Product 1

HCID 587651853-cyclohexyl-N-[(dimethylamino)sulfonyl]-2-(2-formylphenyl)-1H-indole-6-carboxamideYield 210.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-bromo-3-cyclohexyl-N-[(dimethylamino)sulfonyl]-1H-indole-6-carboxamide (950 mg, 2.22 mmol), LiCl (370 mg, 4.44 mmol), tetrakis(triphenylphosphine)palladium(0) (130 mg, 0.11 mmol) in toluene (30 mL) and ethanol (30 mL) containing aqueous 1 N Na2CO3 (15 mL, 15 mmol) was stirred under reflux for 18 hr. The mixture was diluted with ethyl acetate and washed with 1 N HCl (3×) followed by brine (3×). The solution was dried over Na2SO4 and concentrated to dryness to afford the titled compound as a yellow solid (1.06 g, 106%) which contained some triphenyl oxide. The product was used in the following step without additional purification. MS m/z 454 (MH+).

Workup

  1. temperatureunder reflux for 18 hr
  2. washwashed with 1 N HCl (3×)
  3. dry with materialThe solution was dried over Na2SO4
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-99c979dfd9a24e91aefc035c90820b2d
Source dataset
uspto-grants-2008_03
Patent number
US07348425B2

Reaction notes

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