Nitrogen → N-{[6-(hex-1-yn-1-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258563Notes

Reaction equation

HRID 1258563 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.N#N.[CH:26]#[C:27][CH2:28][CH2:29][CH2:30][CH3:31].C(N(C(C)C)C(C)C)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>[C:26]([C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1)#[C:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

9

Reactant 4

HCID 947NitrogenHCID 127321-HexyneHCID 81531DiisopropylethylamineHCID 86653112N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Product 1

HCID 74953678N-{[6-(hex-1-yn-1-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineYield 94.7%

Reagents, catalysts & solvents 4

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

Procedure

To a stirred solution of N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.20 g, 0.536 mmol, 1 eq.) in 2 ml dry THF “degassed” with N2, was added hexyne (0.176 g, 2.14 mmol, 4 eq.) followed by N-ethyldiisopropylamine (0.361 g, 2.79 mmol, 4 eq.), Copper Iodide (0.031 g, 0.161 mmol, 0.3 eq.) and Tetrakis(triphenylphosphine)palladium (0.186 g, 0.161 mmol, 0.3 eq.). The reaction was microwaved 120° C./normal/fixed hold/pre stir 100 s for 180 s. The reaction was diluted with EtOAc and filtered through a “celite” plug. The solvent was evaporated and the residue purified by chromatography on silica gel to give N-{[6-(hex-1-yn-1-yl)pyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.19 g, 85% yield) as a yellow viscous oil.

Workup

  1. customThe reaction was microwaved 120° C./normal/fixed hold/pre
  2. filtrationfiltered through a “celite” plug
  3. customThe solvent was evaporated
  4. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ac8d1c7b571a40cd921e67d47719d0b5
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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