Iodine → HCID 86704621, compound

HRID 1508571Notes

Reaction equation

HRID 1508571 reaction equation
N[C:2]1[CH:3]=[C:4]([C:9]2[C:10]([CH2:17][N:18]3[C@@H:22]([CH3:23])[C@@H:21]([C:24]4[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=4)[O:20][C:19]3=[O:38])=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[F:8].N(OCCCCC)=O.[I:47]I>C(Cl)(Cl)Cl.C(Cl)Cl>[F:35][C:34]([F:37])([F:36])[C:26]1[CH:25]=[C:24]([C@H:21]2[O:20][C:19](=[O:38])[N:18]([CH2:17][C:10]3[C:9]([C:4]4[CH:5]=[CH:6][C:7]([F:8])=[C:2]([I:47])[CH:3]=4)=[CH:14][N:13]=[C:12]([S:15][CH3:16])[N:11]=3)[C@H:22]2[CH3:23])[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=1

Participants

6

Reactant 3

HCID 807IodineHCID 10026Pentyl nitriteHCID 86704619HCID 86704619, compound

Product 1

HCID 86704621HCID 86704621, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the title compound from Step A (2.1 g, 3.75 mmol), n-pentyl nitrite (0.66 g, 5.62 mmol) and I2 (1.24 g, 4.87 mmol) in chloroform (20 mL) was stirred at 80° C. for 1 h. The mixture was cooled, and the solvent was diluted with CH2Cl2. The mixture was washed with Na2S2O3 (5 mL), and with brine (5 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/hexane (10/90) to give the title compound as a yellow gum. 1H NMR (CDCl3, 500 MHz) δ 8.41 (s, 1H), 7.92 (s, 1H), 7.78 (s, 2H), 7.77 (m, 1H), 7.35 (m, 1H), 7.22 (m, 1H), 5.76 (d, J=8.5 Hz, 1H), 4.91 (d, J=17 Hz, 1H), 4.45 (m, 1H), 4.06 (d, J=17.5 Hz, 1H), 2.64 (s, 3H), 0.76 (d, J=7 Hz, 3H). LCMS=672.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. washThe mixture was washed with Na2S2O3 (5 mL)
  3. dry with materialwith brine (5 mL), dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel Biotage 40M
  7. washeluting with EtOAc/hexane (10/90)

Sources & evidence

ORD record
ord-4124e88bc6ed4498a17fa3e80beefa65
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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