Iodine → HCID 131735518, compound

HRID 522210Notes

Reaction equation

HRID 522210 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][C:12]3[C:8]4[C:9](=[N:23][CH:24]=[CH:25][C:7]=4[C:6]=2[CH:26]=1)[N:10]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:11]=3.C([N-]C(C)C)(C)C.[Li+].[I:35]I>O1CCCC1.O1CCCC1.CCCCCCC.C(C1C=CC=CC=1)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][C:12]3[C:8]4[C:9](=[N:23][CH:24]=[CH:25][C:7]=4[C:6]=2[CH:26]=1)[N:10]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=3[I:35]

Participants

6

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 131735519HCID 131735519, compound

Product 1

HCID 131735518HCID 131735518, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 22742125Tetrahydrofuran heptane ethylbenzolSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of Example 14G (310.0 mg, 0.837 mmol) in tetrahydrofuran (8 mL) at −78° C. was added 2M lithium diisopropylamide (1.255 mL, 2.51 mmol) in tetrahydrofuran/heptane/ethylbenzene dropwise. After 60 minutes, a solution of iodine (531 mg, 2.092 mmol) in tetrahydrofuran (3 mL) was cannulated into the reaction mixture and the mixture was stirred at −78° C. for 2 hours. The mixture was quenched with aqueous sodium thiosulfate and extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and purified on silica using the ISCO Companion flash system eluting with heptanes/ethyl acetate (9:1 to 8:2) to provide the title compound. MS (ESI+) m/z 496.8 (M+H)+.

Workup

  1. customThe mixture was quenched 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
  6. custompurified on silica using the ISCO Companion flash system
  7. washeluting with heptanes/ethyl acetate (9:1 to 8:2)

Sources & evidence

ORD record
ord-5f5cfb3385dc4fe4a7f323d1f96d4beb
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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