Sodium Carbonate → (2S)-N-(Cyanomethyl)-4-methyl-2-{[(R)-[4'-(methylthio)-1,1'-biphenyl-4-yl](phenyl)methyl]oxy}pentanamide

HRID 1180418Notes

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.[N].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)CC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=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: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: 100 °C

Procedure

To a solution of (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-N-(cyanomethyl)-4-methylpentanamide (0.84 mmol, 348 mg) in toluene (5 mL) and n-propanol (1.5 mL) was added under a stream of nitrogen 4-(methylthio)phenylboronic acid (1.0 mmol, 169 mg), Pd(PPh3)4 (0.042 mmol, 48 mg), Na2CO3 (2 M, 2 mL). The mixture was degassed with a rapid stream of nitrogen bubbling through the mixture and the mixture was heated to 100° C. for 2 h. The mixture was cooled, diluted with EtOAc and washed with water. The product was isolated by chromatography (40% EtOac/Hexane).

Workup

customThe mixture was degassed with a rapid stream of nitrogen bubbling through the mixture
temperatureThe mixture was cooled
additiondiluted with EtOAc
washwashed with water
customThe product was isolated by chromatography (40% EtOac/Hexane)

Sources & evidence

ORD record: ord-ccd5a2055a2445fc8188b7c25c71efbf
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279478B2

Reaction notes

Loading…