Nitrogen → N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine

HRID 1258562Notes

Reaction equation

HRID 1258562 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]=[C:10]([N:17]2[C:21]([CH3:22])=[N:20][N:19]=[N:18]2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:6]=1.N#N.[CH:25]1([C:28]#[CH:29])[CH2:27][CH2:26]1.C(N(CC)CC)C>C1COCC1.CCOC(C)=O.[Cu](I)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]([N:17]3[C:21]([CH3:22])=[N:20][N:19]=[N:18]3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:6]=2)[CH2:27][CH2:26]1

Participants

9

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 86653111N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine

Product 1

HCID 86653118N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimineYield 56.2%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (0.2 g, 0.527 mmol, 1 eq.) in 3 ml dry THF “degassed” with N2, was added cyclopropylacetylene (0.069 g, 1.05 mmol, 2 eq.) followed by triethylamine (0.213 g, 2.1 mmol, 4 eq.), Copper Iodide (0.015 g, 0.079 mmol, 0.15 eq.) and Tetrakis(triphenylphosphine)palladium (0.030 g, 0.026 mmol, 0.05 eq.). The reaction was stirred for 20 hrs at room temperature for complete conversion. The reaction was diluted with EtOAc (50 ml), filtered through “Chem Elut” cartridge, washed with fresh EtOAc (2×20 ml) and the filtrate was concentrated. The residue was chromatographed on silica gel to give N-{[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]methoxy}-1-(5-methyl-1H-tetrazol-1-yl)-1-phenylmethanimine (0.108 g, 56% yield) as a brown gum.

Workup

  1. filtrationfiltered through “Chem Elut” cartridge
  2. washwashed with fresh EtOAc (2×20 ml)
  3. concentrationthe filtrate was concentrated
  4. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2b3c0044b8b145dea9beee4587a1c898
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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