Sodium Carbonate → HCID 15549970, compound

HRID 844231Notes

Reaction equation

HRID 844231 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.B1([C:22]2[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=2)OCCCO1.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[CH3:14][N:13]([CH2:12][CH2:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH:10]=2)[CH:6]=[CH:7]1)[CH3:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 12992938HCID 12992938, compound

Product 1

HCID 15549970HCID 15549970, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

In a 25 mL round bottom flask equipped with a stir bar was added 6-Bromo-1-(2-(N,N-dimethylamino)ethyl)-1H-indole (0.10 g; 0.37 mmol), pyridine-3-boronic acid-1,3-propanediol cyclic ester (0.12 g; 0.74 mmol), toluene (10 mL), sodium carbonate (2M) (4 mL) and tetrakis(triphenylphosphine)palladium(0) (0.02 g; 0.04 mmol). The reaction mixture was refluxed overnight, filtered through a pad of celite and the solvent evaporated in vacuo. The residue was dissolved in ethyl acetate (30 mL) and successively washed with water (2×20 mL) and brine (20 mL). The organic phase was dried (sodium sulfate), filtered and the solvent was removed in vacuo. The crude residue was purified by column chromatography on silica gel using chloroform:ammonialmethanol (2N) (98:2) to yield the title compound as yellow oil (0.08 g; 85%). 13C NMR (CDCl3): δ 148.6, 147.8, 137.9, 136.5, 134.5, 131.4, 129.3, 128.5, 123.5, 121.6, 118.9, 107.9, 101.3, 59.1, 45.8, 44.8.

Workup

  1. customIn a 25 mL round bottom flask equipped with a stir bar
  2. temperatureThe reaction mixture was refluxed overnight
  3. filtrationfiltered through a pad of celite
  4. customthe solvent evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  6. washsuccessively washed with water (2×20 mL) and brine (20 mL)
  7. dry with materialThe organic phase was dried (sodium sulfate)
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo
  10. customThe crude residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-73fa9718959448ddb31ece174df63296
Source dataset
uspto-grants-2002_04
Patent number
US06380242B1

Reaction notes

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