Cyclopropylacetylene → N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-[3-(methyl-sulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

HRID 1258596Notes

Reaction equation

HRID 1258596 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=2)[C:11]2[N:15]([CH3:16])[N:14]=[N:13][N:12]=2)[N:6]=1.[CH:25]1([C:28]#[CH:29])[CH2:27][CH2:26]1.C1(CNCC2CCCCC2)CCCCC1>O1CCCC1.[Cu]I.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>[CH:25]1([C:28]#[C:29][C:2]2[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=3)[C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[N:6]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 3

HCID 138823CyclopropylacetyleneHCID 4594378Bis(cyclohexylmethyl)amineHCID 86653147N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine

Product 1

HCID 86653148N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-[3-(methyl-sulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimineYield 80%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-[3-(methylsulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine (150 mg, 0.35 mmol), cyclopropylacetylene (8.44 M in toluene, 84 μL, 0.70 mmol), copper(I) iodide (6.72 mg, 0.03 mmol), tetrakis(triphenylphosphine)palladium(0) (20.4 mg, 0.05 mmol), N,N-dicyclohexylmethylamine (0.30 mL, 1.41 mmol) in degassed tetrahydrofuran (3 mL) was stirred under an Argon atmosphere at room temperature for 24 h. After evaporation of the solvent in vacuo, purification on silica gel afforded N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-[3-(methyl-sulfanyl)phenyl]-1-(1-methyl-1H-tetrazol-5-yl)methanimine as a thick oil [116 mg, yield 80%; HPLC/MS: m/z=411 (M+H); logP(HCOOH)=3.99].

Workup

  1. customAfter evaporation of the solvent
  2. customin vacuo, purification on silica gel

Sources & evidence

ORD record
ord-f10e53281c1a43f5971cb3bc4da4764d
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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