Nitrogen → HCID 86653119, compound

HRID 1258564Notes

Reaction equation

HRID 1258564 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][C:3]=1[O:24][CH3:25].N#N.[CH:28]1([C:31]#[CH:32])[CH2:30][CH2:29]1.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>[CH:28]1([C:31]#[C:32][C:2]2[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]3[N:22]([CH3:23])[N:21]=[N:20][N:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][C:3]=2[O:24][CH3:25])[CH2:30][CH2:29]1

Participants

9

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 138823CyclopropylacetyleneHCID 86653120HCID 86653120, compound

Product 1

HCID 86653119HCID 86653119, compoundYield 57.4%

Reagents, catalysts & solvents 4

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

Procedure

To a stirred solution of N-[(6-bromo-5-methoxypyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.150 g, 0.372 mmol, 1 eq.) in 2 ml dry THF “degassed” with N2, was added cyclopropylacetylene (0.073 g, 1.11 mmol, 3 eq.) followed by N-ethyldiisopropylamine (0.191 g, 1.48 mmol, 4 eq.), Copper Iodide (0.010 g, 0.056 mmol, 0.15 eq.) and Tetrakis(triphenylphosphine)palladium (0.042 g, 0.037 mmol, 0.1 eq.). The reaction was microwaved 120° C./normal/fixed hold/pre stir 100 s for 1200 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-(cyclopropylethynyl)-5-methoxypyridin-2-yl]methoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.083 g, 57% 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-4369f822a0614402a611c150ea676402
Source dataset
uspto-grants-2013_06
Patent number
US08466176B2

Reaction notes

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