Diazomethane → HCID 18453546, compound

HRID 1271406Notes

Reaction equation

HRID 1271406 reaction equation
[N+:1](=[CH2:3])=[N-].[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]2=[CH:15][C:16]#N>CCOCC>[Br:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[C:8]12[CH2:16][CH:15]1[C:3]#[N:1]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 69491432HCID 69491432, compound

Product 1

HCID 18453546HCID 18453546, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

An excess of an ethereal diazomethane solution was added portion-wise from a syringe to a suspension of 5-bromo-1,2-dihydro-2-oxo-3H-indol-3-ylidene-acetonitrile (30 mg, 0.1 mmol), prepared as in Example 1, in dry ether (30 mL). The suspension was stirred at 0° C. for 2 hours. Excess diazomethane was quenched with two drops of acetic acid. The reaction mixture was concentrated to dryness in vacuo. The residue was dissolved in toluene (20 mL) and the resulting solution was heated to reflux for 6 hours. Upon removal of the solvents, the solid residue was chromatographed using hexane and ethyl acetate (v/v 1:1) as eluent, providing the title compound in 50% yield (15 mg). MS: m/z 263.2 [M+1]+. 1H NMR (CCl3D): δ 9.06 (br, 1H), 7.45 (m, 1H), 7.30 (br, 1H), 6.87(m, 1H), 2.50 (m, 1H), 2.16 (m, 1H), 1.93 (m, 1H).

Workup

  1. customExcess diazomethane was quenched with two drops of acetic acid
  2. concentrationThe reaction mixture was concentrated to dryness in vacuo
  3. dissolutionThe residue was dissolved in toluene (20 mL)
  4. temperaturethe resulting solution was heated
  5. temperatureto reflux for 6 hours
  6. customUpon removal of the solvents
  7. customthe solid residue was chromatographed

Sources & evidence

ORD record
ord-e731ec5bee064b589b8f65ccc84279ef
Source dataset
uspto-grants-2007_04
Patent number
US07205328B2

Reaction notes

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