Ethyl Acetate → HCID 90020404, compound

HRID 2200135Notes

Reaction equation

[C:1](=[NH:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:22]1[CH:23]=[C:24]([N:32]2[CH2:36][CH:35]([CH3:37])[O:34][C:33]2=[O:38])[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1.CCOC(C)=O>O1CCOCC1.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].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:2]1([C:1](=[N:14][C:22]2[CH:23]=[C:24]([N:32]3[CH2:36][CH:35]([CH3:37])[O:34][C:33]3=[O:38])[CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Add benzophenone imine (3.56 g, 2 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 43 mg, 0.069 mmol), tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 90 mg, 0.098 mmol] and cesium carbonate (858 mg, 2.63 mmol) to the solution of 3-(3-bromo-5-(trifluoromethyl)phenyl)-5-methyloxazolidin-2-one (430 mg, 1.32 mmol) in dioxane (5 mL). Stir the mixture under nitrogen atmosphere at 100° C. overnight. TLC (PE:EtOAc=1:1) shows the reaction is complete. Filter the mixture and concentrate the filtrate to yield the crude product. Purify by flash chromatography (silica gel, PE:EtOAc=1:1) to afford the product (500 mg, 89%).

Workup

filtrationFilter the mixture
concentrationconcentrate the filtrate
customto yield the crude product
customPurify by flash chromatography (silica gel, PE:EtOAc=1:1)

Sources & evidence

ORD record: ord-bd2e85aeee4d453ab014c68c4a41f182
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359338B2

Reaction notes

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