2-Iodoxybenzoic acid → HCID 70008467, compound

HRID 1266040Notes

Reaction equation

HRID 1266040 reaction equation
I(C1C=CC=CC=1C(O)=O)(=O)=O.[OH:13][CH:14]([C:16]1[CH:24]=[CH:23][C:22]2[CH2:25][NH:26][CH2:27][C:28](=[O:29])[N:20]3[C:21]=2[C:17]=1[CH:18]=[CH:19]3)[CH3:15]>CS(C)=O>[C:14]([C:16]1[CH:24]=[CH:23][C:22]2[CH2:25][NH:26][CH2:27][C:28](=[O:29])[N:20]3[C:21]=2[C:17]=1[CH:18]=[CH:19]3)(=[O:13])[CH3:15]

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 69700366HCID 69700366, compound

Product 1

HCID 70008467HCID 70008467, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

o-Iodoxybenzoic acid (Frigerio, et al., J. Org. Chem. 1995, 60, 7272) (2.217 mmol, 0.621 g) was added to a solution of 7-(1-Hydroxy-ethyl)-3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 163) (0.739 mmol, 0.170 g) in DMSO (8 mL) at rt. The reaction mixture was stirred at rt for 2.5 h. The solvent was removed in vacuo and the residue was taken up in EtOAc and washed with 5% Na2S2O3/5% NaHCO3, H2O and brine. The organic layer was dried over anhydrous MgSO4 and concentrated to give an orange solid. The solid was purified by flash silica gel chromatography eluting with a gradient of 0-5% MeOH in CHCl3 to give 0.094 g (75%) of a pale pink solid: mp=285-287° C.; 1H NMR (DMSO-d6) δ 2.42 (s, 3H), 3.56-3.61 (m, 2H), 4.44 (br s, 2H), 7.32 (t, 1H, J=6.0 Hz), 7.92 (d, 1H, J=6.0 Hz), 8.40-8.44 (m, 3H); HRMS calcd. for C13H12N2O2 (M+) 228.0899, found (M+) 228.0890; Anal. (C13H12N2O2) C, H, N.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with 5% Na2S2O3/5% NaHCO3, H2O and brine
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customto give an orange solid
  6. customThe solid was purified by flash silica gel chromatography
  7. washeluting with a gradient of 0-5% MeOH in CHCl3

Sources & evidence

ORD record
ord-db0dec57e02048abae4f1d1a74136045
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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