Chlorotrimethylsilane → HCID 59633933, compound

HRID 1615052Notes

Reaction equation

HRID 1615052 reaction equation
[Cl-].[Li+].BrC(Br)C.Cl[Si](C)(C)C.[C:12]([N:19]1[CH2:22][CH:21](I)[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH:24]1([C:27]2[CH:43]=[CH:42][C:30]([CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36](I)=[CH:35][C:34]=3[O:40][CH3:41])=[CH:29][CH:28]=2)[CH2:26][CH2:25]1>O1CCCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[CH:24]1([C:27]2[CH:43]=[CH:42][C:30]([CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36]([CH:21]4[CH2:22][N:19]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:20]4)=[CH:35][C:34]=3[O:40][CH3:41])=[CH:29][CH:28]=2)[CH2:25][CH2:26]1

Participants

9

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 112011,1-DibromoethaneHCID 433294Lithium ChlorideHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylateHCID 59634051HCID 59634051, compound2×

Product 1

HCID 59633933HCID 59633933, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent3×HCID 178419050HCID 178419050, compoundSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of zinc (3.0 g) and lithium chloride (1.5 g) in THF (25 mL) were added dibromoethane (0.30 mL) and chlorotrimethylsilane (0.44 mL) at 70° C. under argon atmosphere. The mixture was stirred at 70° C. for 10 min. A solution of 1-Boc-3-iodoazetidine (9.8 g) in THF (10 mL) was added dropwise to the mixture at RT. The mixture was stirred at RT for 1 hr. To the mixture were added a solution of 1-(4-cyclopropylbenzyloxy)-4-iodo-2-methoxybenzene (5.3 g) prepared in (3) in THF (15 mL) and bis(triphenylphosphine)palladium (II) dichloride (0.49 g). The reaction mixture was stirred at RT for 3 hr. The reaction mixture was quenched with saturated aqueous NH4C1 and extracted with ethyl acetate. The organic layer was dried over MgSO4. The solvent was removed under reduced pressure. The residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1 to 4/1) to give the title compound.

Workup

  1. stirringThe mixture was stirred at RT for 1 hr
  2. stirringThe reaction mixture was stirred at RT for 3 hr
  3. customThe reaction mixture was quenched with saturated aqueous NH4C1
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1 to 4/1)

Sources & evidence

ORD record
ord-4264a397a6c64c33ab8867c63fcb3112
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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