Tris(1,1-dimethylethyl)phosphine → HCID 57094554, compound

HRID 844251Notes

Reaction equation

HRID 844251 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[NH2:16][CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1.CC(C)([O-])C.[Na+].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Pd]>[NH2:16][CH:17]1[CH2:21][CH2:20][N:19]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=2)[CH2:18]1

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 1644013-AminopyrrolidineHCID 12992938HCID 12992938, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 57094554HCID 57094554, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of the 6-bromo-1-((N,N-dimethylamino)ethyl)-1H-indole (54 mg, 0.2 mmol), 3-aminopyrrolidine (6 equiv.) and sodium t-butoxide (1.4 equiv.) in xylene was added palladium acetate and P(t-Bu)3 (P/Pd=4). The mixture was heated at 120° C. overnight. The reaction was then poured into ice-cold water followed by extraction with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, and dried over Na2SO4 (anhydrous). The organic layer was concentrated in vacuo and purified by flash column chromatography yielding 6-[3-Aminopyrrolidin-1-yl]-1-((N,N-dimethylamino)ethyl)-1H-indole: (43 mg of a yellow oil, 80%).

Workup

  1. additionThe reaction was then poured into ice-cold water
  2. extractionfollowed by extraction with ethyl acetate (2×50 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4 (anhydrous)
  5. concentrationThe organic layer was concentrated in vacuo
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-98d66c7634f34ec1811ab2ad12b9c8b2
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

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