N-Iodosuccinimide → HCID 58404694, compound

HRID 1253560Notes

Reaction equation

HRID 1253560 reaction equation
[CH2:1]([O:8][C:9]1[N:14]2[CH:15]=[CH:16][N:17]=[C:13]2[CH:12]=[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:24]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[N:14]2[C:15]([I:24])=[CH:16][N:17]=[C:13]2[CH:12]=[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 58404774HCID 58404774, compound2×

Product 1

HCID 58404694HCID 58404694, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(benzyloxy)-7-phenylimidazo[1,2-a]pyridine (Compound 11-1) (60 mg, 0.20 mmol) in acetonitrile (4 mL) was added N-iodosuccinimide (59 mg, 0.26 mmol) at room temperature. The reaction was stirred at room temperature for 12 h, diluted with ethyl acetate, and washed with 1N aqueous sodium hydroxide. The organic layer was separated, and the aqueous layer was back extracted one time with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to give 5-(benzyloxy)-3-iodo-7-phenylimidazo[1,2-a]pyridine. 1H NMR (500 MHz, CDCl3) δ 7.55-7.59 (m, 4H), 7.54 (s, 1H), 7.36-7.47 (m, 7H), 6.34 (s, 1H), 5.34 (s, 2H). LRMS (ESI) calculated for C20H16IN2O [M+H]+, 427.0; found 426.9.

Workup

  1. washwashed with 1N aqueous sodium hydroxide
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back extracted one time with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record
ord-fd19da58b54c4495917da7a1f11f3cb8
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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