Iodine → HCID 9895034, compound

HRID 376225Notes

Reaction equation

HRID 376225 reaction equation
[I:1]I.N[C:4]1[C:8]([CH:9]2[CH2:11][C:10]2([Br:13])[Br:12])=[CH:7][N:6]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:5]=1.N(OC(C)(C)C)=O>ClCCl>[Br:12][C:10]1([Br:13])[CH2:11][CH:9]1[C:8]1[C:4]([I:1])=[N:5][N:6]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 9913636HCID 9913636, compound

Product 1

HCID 9895034HCID 9895034, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodine (0.55 g) was added to a stirred solution of the title compound of Example 8 (0.40 g) in dichioromethane (10 ml), followed by the dropwise addition of t-butyl nitrite (0.21 g). The reaction mixture was stirred at room temperature for 2 hours, then partitioned between dichloromethane and aqueous sodium thiosulphate solution and the organic phase separated, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using hexane and then dichloromethane as eluants, followed by reverse phase HPLC on C18 silica, using a mixture of acetonitrile:water:methanol (30:60:10) as eluant, to produce the title compound as an off-white foam. δ (CDCl3): 1.84 (t,1H), 2.26 (dd,1H), 2.67 (dd,1H), 7.20 (s,1H), 7.72 (s,2H). MS (thermospray): M/Z [M+H] 602.4; C13H6Br2Cl2F3IN2 +H requires 602.74.

Workup

  1. custompartitioned between dichloromethane and aqueous sodium thiosulphate solution
  2. customthe organic phase separated
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. additiona mixture of acetonitrile:water:methanol (30:60:10) as eluant

Sources & evidence

ORD record
ord-a1ae7e4e3c7944109da076273bc58ae6
Source dataset
uspto-grants-2000_02
Patent number
US06019986

Reaction notes

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