Iodine → HCID 90412233, compound

HRID 1521952Notes

Reaction equation

HRID 1521952 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[CH:15]=[CH:16][C:9]=23)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[I:36]I>O1CCCC1.O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:26][CH3:27])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)(=[O:19])=[O:18])[C:15]([I:36])=[CH:16][C:9]=23)[CH:7]=1

Participants

6

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 90411876HCID 90411876, compound

Product 1

HCID 90412233HCID 90412233, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of Example 87A (4.24 g, 11.09 mmol) in tetrahydrofuran at −78° C. was added dropwise 2M lithium diisopropylamide (8.32 mL, 16.63 mmol) in tetrahydrofuran/heptane/ethylbenzene. After 30 minutes, iodine (5.63 g, 22.18 mmol) in tetrahydrofuran (50 mL) was cannulated into the mixture. The mixture was stirred at −78° C. for 3 hours, quenched with aqueous sodium thiosulfate and extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated until a precipitate formed. The solids were filtered, washed with ethyl acetate and dried under vacuum to afford the title compound. MS (ESI+) m/z 508.9 (M+H)+.

Workup

  1. customquenched with aqueous sodium thiosulfate
  2. extractionextracted with ethyl acetate (twice)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated until a precipitate
  6. customformed
  7. filtrationThe solids were filtered
  8. washwashed with ethyl acetate
  9. customdried under vacuum

Sources & evidence

ORD record
ord-0fd3e9c696d04da0b7da5d983addc966
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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