Potassium Carbonate → HCID 22676726, compound

HRID 1006247Notes

Reaction equation

HRID 1006247 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12]Br.[CH2:17]([O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:28]2[Br:39])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.O>[CH2:17]([O:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH2:12][C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([O:8][CH3:7])[CH:10]=1)[C:29]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:28]2[Br:39])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 40672073-Methoxybenzyl bromideHCID 22676785HCID 22676785, compound

Product 1

HCID 22676726HCID 22676726, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Powdered potassium carbonate (2.79 g, 20.2 mmol) and 3-methoxybenzyl bromide (2.03 g, 10.1 mmol) were added successively to a stirred solution of ethyl 5-(benzyloxy)-3-bromo-1H-indole-2-carboxylate, Lit. WO96/18393 (3.63 g, 9.70 mmol) in N,N-dimethylformamide (20 mL). The reaction was stirred for 23 h and then diluted with water (250 mL). The product was extracted with ethyl acetate (3×100 mL) and then the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Recrystalization of the residue using methanol afforded 4.03 g (84%) of the desired product. The product had: 1H NMR (300 MHz, CDCl3) δ 7.05-7.91 (m, 9 H), 6.74 (dd, 1 H), 6.53-6.63 (m, 2 H), 5.37 (s, 2 H), 4.37 (q, 2 H), 3.71 (s, 3 H), 1.39 (t, 3 H); mass spectroscopy gave MH+=494.1 (calc'd exact mass for C26H24BrNO4=493.09).

Workup

  1. extractionThe product was extracted with ethyl acetate (3×100 mL)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customRecrystalization of the residue

Sources & evidence

ORD record
ord-35b74885eddd4605aedb1ab714620d0b
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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