Chlorotrimethylsilane → HCID 57470079, compound

HRID 2262619Notes

Reaction equation

HRID 2262619 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10](I)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrCCBr.C[Si](Cl)(C)C.Br[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 114661-Bromo-4-nitrobenzeneHCID 521585Tris(furan-2-yl)phosphaneHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 1

HCID 57470079HCID 57470079, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Following the same procedure as described in 46.3, the organozinc species was prepared using 3-iodo-azetidine-1-carboxylic acid tert-butyl ester (1.74 g, 6.14 mmol), Zn dust (520 mg, 7.95 mmol), 1,2 dibromoethane (84 μl, 0.97 mmol) and trimethylsilyl chloride (115 μl, 0.92 mmol). It was then coupled with 1-bromo-4-nitrobenzene (1.24 g, 6.13 mmol) using Pd2(dba)3 (90 mg, 0.10 mmol) and P(2-furyl)3 (85 mg, 0.36 mmol). Purification of the crude product by flash column chromatography (heptane:ethyl acetate, 4:1) provides the title compound (880 mg, 52%) as a light yellow oil.

Workup

  1. customPurification of the crude product by flash column chromatography (heptane:ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-6bff60d2c5d147bdb253fca67469260f
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

Loading…