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

HRID 1258561Notes

Reaction equation

HRID 1258561 reaction equation
Br[C:2]1[S:3][C:4]([CH3:23])=[C:5]([CH2:7][O:8][N:9]=[C:10]([C:17]2[N: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:26]#[C:27][CH2:28][CH2:29][CH3:30].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>[CH3:23][C:4]1[S:3][C:2]([C:26]#[C:27][CH2:28][CH2:29][CH3:30])=[N:6][C:5]=1[CH2:7][O:8][N:9]=[C:10]([C:17]1[N:21]([CH3:22])[N:20]=[N:19][N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 123091-PentyneHCID 86653110N-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 86653117N-{[5-methyl-2-(pent-1-yn-1-yl)-1,3-thiazol-4-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineYield 72.8%

Reagents, catalysts & solvents 4

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

Procedure

To a stirred solution of N-[(2-bromo-5-methyl-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0.509 mmol, 1 eq.) in 3 ml dry THF “degassed” with N2, was added pentyne (0.069 g, 1.01 mmol, 2 eq.) followed by triethylamine (0.205 g, 2.03 mmol, 4 eq.), Copper Iodide (0.014 g, 0.076 mmol, 0.15 eq.) and Tetrakis(triphenylphosphine)palladium (0.029 g, 0.025 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 evaporated. The residue was chromatographed on silica gel to give N-{[5-methyl-2-(pent-1-yn-1-yl)-1,3-thiazol-4-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.141 g, 69% yield) as a brown gum.

Workup

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

Sources & evidence

ORD record
ord-549e6e5a003f43498cbb96299d7ff1c5
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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