4-Fluoroiodobenzene → HCID 10500757, compound

HRID 481343Notes

Reaction equation

HRID 481343 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([Cl:21])[CH:19]=2)[NH:14][CH:13]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+].CN1CCCC1=O>O>[CH2:1]([N:8]([CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([Cl:21])[CH:19]=2)[N:14]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[CH:13]=1)[CH3:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 10518227HCID 10518227, compound

Product 1

HCID 10500757HCID 10500757, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of N-benzyl-N-methyl-2-(5-chloro-3-1H-indolyl)ethylamine (16 g, 0.054 mol), 4-fluoro-iodobenzene (14.3 g, 0.064 mol), K2CO3 (11.1 g, 0.080 mol) and 1-methyl-2-pyrrolidinone (200 mL) was heated at 165° C. for 8 h. After cooling to room temperature water (250 mL) was added and the thus formed mixture was extracted with diethyl ether (2×300 mL). The combined organic phases were washed with brine (3×500 mL) and dried (Na2SO4). Evaporation of the solvent afforded an oil that was purified by column chromatography (eluted with ethyl acetate/heptane 1:3) affording pure title compound as an oil: 13.7 g (26%) 1H NMR (CDCl3) δ 2.35 (s, 3 H), 2.70-2.80 (m, 2 H), 2.90-3.00 (m, 2 H), 3.60 (s, 2 H), 7.05-7.40 (m, 12 H), 7.55 (broad s, 1 H).

Workup

  1. additionwas added
  2. extractionthe thus formed mixture was extracted with diethyl ether (2×300 mL)
  3. washThe combined organic phases were washed with brine (3×500 mL)
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customafforded an oil that
  7. customwas purified by column chromatography (eluted with ethyl acetate/heptane 1:3)

Sources & evidence

ORD record
ord-d4c0e9bf34de4385bb81b2becb823911
Source dataset
uspto-grants-1998_08
Patent number
US05789404

Reaction notes

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