Cesium carbonate → HCID 67104954, compound

HRID 1173604Notes

Reaction equation

HRID 1173604 reaction equation
[Si:1]([O:8][CH:9]1[C:13]2([CH2:15][CH2:14]2)[C:12](=[O:16])[NH:11][C@H:10]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:1]([O:8][C@H:9]1[C:13]2([CH2:14][CH2:15]2)[C:12](=[O:16])[N:11]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[CH:20]=2)[C@H:10]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:1]([O:8][C@@H:9]1[C:13]2([CH2:14][CH2:15]2)[C:12](=[O:16])[N:11]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([Cl:27])[CH:20]=2)[C@H:10]1[CH3:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 70104204-Bromo-2-chlorobenzonitrileHCID 58238347HCID 58238347, compound

Product 2

HCID 59556888HCID 59556888, compoundYield 22.2%HCID 67104954HCID 67104954, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

Using (6S)-7-(tert-butyldimethylsilyloxy)-6-methyl-5-azaspiro[2.4]heptan-4-one (200.8 mg), 4-bromo-2-chlorobenzonitrile (194.3 mg), cesium carbonate (384 mg), tris(dibenzylideneacetone)dipalladium(0) (36 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (91 mg), and in the same manner as in Reference Example 3, the title compound (yield: 68.4 mg, yield: 22.2%) and 4-[(6S,7R)-7-(tert-butyldimethylsilyloxy)-6-methyl-4-oxo-5-azaspiro[2.4]hept-5-yl]-2-chlorobenzonitrile (yield: 161 mg, yield: 52.4%) were obtained each as a colorless solid.

Sources & evidence

ORD record
ord-dac64c36ed314e5e9fd26e0930ecc907
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

Loading…