p-Xylyl bromide → HCID 21964305, compound

HRID 2373469Notes

Reaction equation

HRID 2373469 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2.[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1>CN(C=O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:18][C:19]1[CH:26]=[CH:25][C:22]([CH3:23])=[CH:21][CH:20]=1)[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7]2

Participants

5

Reactant 3

HCID 7721p-Xylyl bromideHCID 24758Sodium hydrideHCID 259091Ethyl 5-Bromoindole-2-carboxylate

Product 1

HCID 21964305HCID 21964305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (60%, 3.88 g, 96.98 mmol) was added portionwise to a stirring solution of ethyl 5-bromo-1H-indole-2-carboxylate (20.0 g, 74.6 mmol) in DMF (140 mL) at 0° C. under a nitrogen atmosphere over a period of 10 min. The mixture was then warmed to room temperature. After the reaction mixture was stirred at room temperature for one hour, 4-methylbenzyl bromide (14.2 g, 74.6 mmol) was added and the mixture was stirred at room temperature overnight. The reaction was quenched with aqueous ammonium chloride and diluted with water. The aqueous mixture was extracted with ethyl acetate. The organic extract was washed with water and brine, dried over anhydrous magnesium sulfate. This mixture was concentrated to give a semi-solid contained 0.8 mole equivalent DMF. Mass spectrum (ESI, [M+H]+) m/z 372. 1H NMR (400 MHz, DMSO-d6) δ 7.93 (d, 1H, J=7.94 Hz), 7.55 (d, 1H, J=9.01 Hz), 7.40 (dd, 1H, J=8.85 and 1.98 Hz), 7.32 (s, 1H), 7.04 (d, 2H, J=7.96 Hz), 6.90 (d, 2H, J=7.94 Hz), 5.79 (s, 2H), 4.28 (q, 2H), 2.20 (s, 3H), and 1.28 ppm (t, 3H).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. additiondiluted with water
  4. extractionThe aqueous mixture was extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThis mixture was concentrated
  9. customto give a semi-solid

Sources & evidence

ORD record
ord-f9206b246fa9439495b9a3ce4b452c8b
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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