Iodine → HCID 90412829, compound

HRID 1522024Notes

Reaction equation

HRID 1522024 reaction equation
[F:1][C:2]1[C:3]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])=[C:4]2[C:10]([C:11]#[N:12])=[CH:9][N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:5]2=[N:6][CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[I:38]I>O1CCCC1>[F:1][C:2]1[C:3]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])=[C:4]2[C:10]([C:11]#[N:12])=[C:9]([I:38])[N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 90412488HCID 90412488, compound

Product 1

HCID 90412829HCID 90412829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-75 °C

Procedure

A solution of Example 263D (0.72 g, 1.7 mmol) in tetrahydrofuran (50 mL) was cooled to −75° C. and 2N lithium diisopropylamide (2.6 mL, 5.2 mmol) was added dropwise. The mixture was stirred at −75° C. for 30 minutes and a solution of iodine (0.88 g, 3.47 mmol) in tetrahydrofuran (2.5 mL) was added. The mixture was slowly brought to room temperature, quenched with aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (twice). The organic phase was concentrated and purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 542 (M+H)+.

Workup

  1. customwas slowly brought to room temperature
  2. customquenched with aqueous ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (twice)
  4. concentrationThe organic phase was concentrated
  5. custompurified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4cc99239ef354c53b990645d6f0baf08
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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