Sodium Carbonate → HCID 15549970, compound

HRID 988089Notes

Reaction equation

HRID 988089 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)OCC[CH2:18][O:17]1.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>[NH3:8].[CH3:18][OH:17].[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

7

Reactant 3

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

Product 2

HCID 15549970HCID 15549970, compoundYield 163%HCID 21705897Ammonia methanol

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:ammonia/methanol (2N) (98:2) to yield the title compound as yellow oil (0.08 g; 85%). 13C NMR (CDCl3): δ148.6, 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-8c9b9e7ec0f14eb598d17e3a20be1901
Source dataset
uspto-grants-2003_10
Patent number
US06635639B2

Reaction notes

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