Iodine → HCID 69700895, compound

HRID 1266015Notes

Reaction equation

HRID 1266015 reaction equation
[C:1]1(=[O:14])[N:12]2[C:13]3[C:9]([CH:10]=[CH:11]2)=[CH:8][CH:7]=[CH:6][C:5]=3[CH2:4][NH:3][CH2:2]1.[OH-].[K+].[I:17]I>CN(C=O)C>[I:17][C:8]1[CH:7]=[CH:6][C:5]2[CH2:4][NH:3][CH2:2][C:1](=[O:14])[N:12]3[C:13]=2[C:9]=1[CH:10]=[CH:11]3

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 69701319HCID 69701319, compound

Product 1

HCID 69700895HCID 69700895, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a pale-yellow solution of 3,4-dihydro-2H-[1,4]diazepino[6,7,1-hi]indol-1-one (Example 42, 0.051 g, 0.274 mmol) in 5 mL DMF was added KOH (0.058 g, 1.03 mmol) and iodine (0.139 g, 0.548 mmol) at rt. The reaction mixture was stirred at rt overnight, at which time solvent was removed in vacuo. The residue was taken up in EtOAc and washed with 0.1% aq sodium bisulfite, H2O and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated to give 0.078 g (92%) of a pale-yellow solid: 1H NMR (DMSO-d6) δ 3.56-3.59 (m, 2H), 4.40 (m, 2H), 7.26 (t, 1H, J=7.5 Hz), 7.52 (d, 1H, J=7.5 Hz), 7.67 (s, 1H), 7.93 (d, 1H, J=7.5 Hz), 8.37 (t, 1H, J=5.3 Hz). HRMS calcd. for C11H9N2OI (M+) 311.9761, found 311.9776. Anal. (C11H9N2OI) C, H, N.

Workup

  1. customwas removed in vacuo
  2. washwashed with 0.1% aq sodium bisulfite, H2O and brine
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-955c2358e3cf44dd933a10656cab2cbd
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

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