Imidazole → 5-Iodomethyl-2-phenyl-7-nitro-1H-indole

HRID 2089591Notes

Reaction equation

HRID 2089591 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:6]2.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:45]I>C1COCC1>[I:45][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH:8][C:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:6]2

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 684763775-Hydroxymethyl-2-phenyl-7-nitro-1H-indole

Product 1

HCID 684702645-Iodomethyl-2-phenyl-7-nitro-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Hydroxymethyl-2-phenyl-7-nitro-1H-indole (804 mg, 3 mmol) prepared in Step A of Example 29 was dissolved in THF (10 mL), and imidazole (408 mg, 6 mmol) and triphenylphosphine (1.52 g, 6 mmol) were added thereto. Iodine (453 mg, 3.9 mmol) was added to the mixture, which was then stirred for 2 h. After completion of the reaction, the reaction mixture was filtered through a cellite, and the product was used in the next reaction without further purification.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through a cellite
  3. customthe product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-815bd473d8694f55b28d3b0135bd2790
Source dataset
uspto-grants-2013_05
Patent number
US08436038B2

Reaction notes

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