Carbonate Ion → HCID 22032934, compound

HRID 2221184Notes

Reaction equation

HRID 2221184 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[Na].C(=O)([O-])[O-]>O.C(O)C.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][N:8]3[CH3:11])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 19660Carbonate IonHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 5360545SodiumHCID 155468546-Bromo-1-methyl-1H-indole

Product 1

HCID 22032934HCID 22032934, compoundYield 51%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The mixture of 6-bromo-1-methyl-1H-indole (0.216 g, 1.03 mmol), 4-trifluoromethylbenzeneboronic acid (0.216 g, 1.14 mmol), tetrakis(triphenylphosphine) palladium (0.0541 g, 0.0468 mmol) and sodium, carbonate (0.438 g, 4.13 mmol) in water (2.5 mL), ethanol (1 mL) and toluene (5 mL) was refluxed for 1.6 hours. The mixture was cooled to room temperature then evaporated to dryness. The residue was partitioned in methylene chloride and water. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was purified by flash chromatography using 0-0.2% ethyl acetate in hexane as an eluant to give the title compound (0.144 g, 51%) as a white solid, mp: ˜100° C.; 1HNMR (200 MHz, DMSO-d6): δ8.0 (d, 2H, J=6.6 Hz), 7.8 (d, 3H, J=8.7 Hz), 7.65 (d, 1H, J=8.7 Hz), 7.35-7.5 (m, 2 H), 6.45 (d, 1H, J=2.6 Hz), and 3.8-3.95 ppm (m, 3H).

Workup

  1. temperaturewas refluxed for 1.6 hours
  2. customthen evaporated to dryness
  3. customThe residue was partitioned in methylene chloride
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a30e0fcaaa014cbbb2c7c1c7555e90a6
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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