Tetramethyltin → (R,R)-N-[3-(4-ethoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide

HRID 2422721Notes

Reaction equation

[Sn](C)(C)(C)[CH3:2].Br[C:7]1[C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH3:27])=[CH:21][CH:20]=2)=[N:9][S:10][C:11]=1[NH:12][C:13]([C@@H:15]1[CH2:17][C@H:16]1[CH3:18])=[O:14]>CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:8]2[C:7]([CH3:2])=[C:11]([NH:12][C:13]([C@@H:15]3[CH2:17][C@H:16]3[CH3:18])=[O:14])[S:10][N:9]=2)=[CH:20][CH:21]=1)[CH3:27]

Participants

Conditions

Temperature: 130 °C

Procedure

Add PdCl2(PPh3)2 (0.07 g, 0.09 mmol) and Sn(CH3)4 (0.34 mL, 0.44 g, 2.48 mmol) to (R,R)—N-[4-bromo-3-(4-ethoxyphenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide (0.24 g, 0.62 mmol) in DMF (1 mL) and stir the reaction mixture at 130° C. in a sealed tube overnight. Dilute with EtOAc (100 mL) and brine (100 mL). Collect the organic phase, dry (MgSO4), and evaporate. Filter over silica gel and wash with EtOAc. Evaporate and crystallize from EtOAc/hexane to afford (R,R)—N-[3-(4-ethoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide. Yield: 81.7%.

Workup

customCollect the organic phase
dry with materialdry (MgSO4)
customevaporate
filtrationFilter over silica gel
washwash with EtOAc
customEvaporate
customcrystallize from EtOAc/hexane

Sources & evidence

ORD record: ord-b6d5b3ed8e984b179def2ad63ebc345b
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960419B2

Reaction notes

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