Iodoethane → HCID 10361797, compound

HRID 915507Notes

Reaction equation

HRID 915507 reaction equation
[CH:1](N(C(C)C)CC)(C)[CH3:2].[CH2:10](I)[CH3:11].[CH3:13][NH:14][C:15]([C:17]1[C:21]2[CH:22]=[C:23]([O:27][CH:28]([CH3:30])[CH3:29])[C:24]([NH2:26])=[CH:25][C:20]=2[O:19][C:18]=1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)=[O:16]>C(#N)C>[CH3:13][NH:14][C:15]([C:17]1[C:21]2[CH:22]=[C:23]([O:27][CH:28]([CH3:30])[CH3:29])[C:24]([NH:26][CH2:1][CH3:2])=[CH:25][C:20]=2[O:19][C:18]=1[C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)=[O:16].[CH3:13][NH:14][C:15]([C:17]1[C:21]2[CH:22]=[C:23]([O:27][CH:28]([CH3:30])[CH3:29])[C:24]([N:26]([CH2:10][CH3:11])[CH2:1][CH3:2])=[CH:25][C:20]=2[O:19][C:18]=1[C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)=[O:16]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 10450038HCID 10450038, compound

Product 2

HCID 10361797HCID 10361797, compoundYield 45%HCID 10430981HCID 10430981, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diisopropylethylamine (407 μL, 2.34 mmol) and ethyl iodine (187 μL, 2.34 mmol) were added to a solution of 6-amino-2-(4-fluoro-phenyl)-5-isopropoxy-benzofuran-3-carboxylic acid methylamide, prepared according to Example 16 (200 mg, 584 μmol) in dry acetonitrile (8 mL). The reaction was monitored under analytical LC/MS conditions and quenched by addition of water (4 mL). After concentration to dryness, the crude product was purified by preparative HPLC (reverse phase C18, acetonitrile/water plus 0.1% acetic acid), affording 97 mg (45%) of the 6-ethylamino-2-(4-fluoro-phenyl)-5-isopropoxy-benzofuran-3-carboxylic acid methylamide and 63 mg (27%) of 6-diethylamino-2-(4-fluoro-phenyl)-5-isopropoxy-benzofuran-3-carboxylic acid methylamide.

Workup

  1. customprepared
  2. customquenched by addition of water (4 mL)
  3. concentrationAfter concentration to dryness
  4. customthe crude product was purified by preparative HPLC (reverse phase C18, acetonitrile/water plus 0.1% acetic acid)

Sources & evidence

ORD record
ord-2a5842d5c0424a2786c1eed76bf4c922
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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