Iodoethane → HCID 10361797, compound

HRID 1445519Notes

Reaction equation

HRID 1445519 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-4f5ca5088e284fa3897e6b4b55d26fce
Source dataset
uspto-grants-2010_02
Patent number
US07666863B2

Reaction notes

Loading…