Aniline → HCID 23152808, compound

HRID 1012275Notes

Reaction equation

HRID 1012275 reaction equation
Br[C:2]1[N:3]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[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]([O:19][CH3:20])=[O:18])[CH:5]=2.[C:28]1([NH2:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[Cl-:35].[Li+].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>COCCOC.O.[Pd].C(OCC)(=O)C>[NH2:34][C:28]1[CH:33]=[C:32]([Cl:35])[CH:31]=[CH:30][C:29]=1[C:2]1[N:3]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2

Participants

10

Reactant 5

HCID 6115AnilineHCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 23152411HCID 23152411, compound

Product 1

HCID 23152808HCID 23152808, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of methyl 2-bromo-3-cyclohexyl-1-(2-ethoxycarbonylethyl)-1H-indole-6-carboxylate (1.00 g, 2.29 mmol) and 2-dioxaborolan-2-yl)phenylamine (697 mg, 2.75 mmol) in 1,2-dimethoxyethane (12 ml) and water (6 ml) were added lithium chloride (291 mg, 6.87 mmol), sodium carbonate (729 mg, 6.87 mmol) and tetrakis(triphenyl)phosphine)palladium (265 mg, 0.229 mmol), and the mixture was stirred at 90° C. for 3.5 hr. The mixture was allowed to cool to room temperature and saturated aqueous ammonium chloride solution and ethyl acetate were added. The mixture was filtered through celite, and the filtrate was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:acetone=3:1) to give methyl 2-(2-amino-4-chlorophenyl)-3-cyclohexyl-1-(2-ethoxycarbonylethyl)-1H-indole-6-carboxylate (1.10 g, yield 100%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was filtered through celite
  3. washthe filtrate was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (hexane:acetone=3:1)

Sources & evidence

ORD record
ord-9e2a6059559a4c7992f5f2b11396226b
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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