Potassium Iodide → (2S)-N-(cyanomethyl)-4-methyl-2-{[(R)-{4-[4-(methylthio)benzoyl]phenyl}(phenyl)methyl]oxy}pentanamide

HRID 1180434Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:9][C@@H:10]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:11]([NH:13][CH2:14][C:15]#[N:16])=[O:12])=[CH:4][CH:3]=1.[CH3:27][S:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.[I-].[K+].[C:40](=O)([O-])[O-:41].[K+].[K+]>C1(OC)C=CC=CC=1>[C:15]([CH2:14][NH:13][C:11](=[O:12])[C@@H:10]([O:9][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([C:40](=[O:41])[C:32]2[CH:33]=[CH:34][C:29]([S:28][CH3:27])=[CH:30][CH:31]=2)=[CH:3][CH:4]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:17][CH:18]([CH3:20])[CH3:19])#[N:16]

Participants

Conditions

Temperature: 90 °C

Procedure

(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide from example 68 (150 mg, 0.361 mmol), 4-(methylthio)phenyl boronic acid (67 mg, 0.398 mmol, 1.1 eg), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II)complex) (7.9 mg, 0.011 mmol, 0.03 eg), potassium iodide (180 mg, 1.08 mmol, 3 eg), potassium carbonate (149 mg, 1.08 mmol, 3 eg) were mixed together in anisole (5 mL). The reaction mixture was degased 3× with nitrogen, then heated at 90° C. under latm of CO for 18 hours. The crude reaction mixture was concentrated under high vacuum and the residue was chromatographed with 30% EtOAc/hexane to give the title compound.

Workup

customThe reaction mixture was degased 3× with nitrogen
customThe crude reaction mixture
concentrationwas concentrated under high vacuum
customthe residue was chromatographed with 30% EtOAc/hexane

Sources & evidence

ORD record: ord-9ed0d3bb45394bfc9693363812d85341
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279478B2

Reaction notes

Loading…