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

HRID 2422721
Notes
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Reaction equation

HRID 2422721 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 11661TetramethyltinHCID 67180534(R,R)-N-[4-bromo-3-(4-ethoxyphenyl)isothiazol-5-yl]-2-methylcyclopropane-carboxamide

Product 1

HCID 67181122(R,R)-N-[3-(4-ethoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamideYield 81.7%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalyst
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent
HCID 57417360Sodium chloride; waterSolvent

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

  1. customCollect the organic phase
  2. dry with materialdry (MgSO4)
  3. customevaporate
  4. filtrationFilter over silica gel
  5. washwash with EtOAc
  6. customEvaporate
  7. 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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