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

HRID 1042342

反応式

HRID 1042342 の反応式
Br[C:2]1[S:3][CH:4]=[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:25]1([C:28]#[CH:29])[CH2:27][CH2:26]1.[CH2:30](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:25]1([C:28]#[C:29][C:2]2[S:3][CH:4]=[C:5]([CH:7]([O:8][N:9]=[C:10]([C:17]3[N:21]([CH3:22])[N:20]=[N:19][N:18]=3)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:30])[N:6]=2)[CH2:27][CH2:26]1

参加物

9

反応物 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 138823CyclopropylacetyleneHCID 86649974N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

生成物 1

HCID 74954639N-{1-[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]ethoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine収率 51.5%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of N-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.15 g, 0.38 mmol, 1 eq.) in 2 ml dry THF “degassed” with N2, was added Cyclopropylacetylene (70%, 0.144 g, 1.52 mmol, 4 eq.) followed by N-ethyldiisopropylamine (0.256 g, 1.98 mmol, 5.2 eq.), Copper Iodide (0.022 g, 0.1141 mmol, 0.3 eq.) and Tetrakis(triphenylphosphine)palladium (0.132 g, 0.114 mmol, 0.2 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 was purified by chromatography on silica gel to give N-{1-[2-(cyclopropylethynyl)-1,3-thiazol-4-yl]ethoxy}-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.074 g, 48% yield) as a yellow viscous oil.

後処理

  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 was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-ed3c863ec1fb4367bcf64a918c23dbe1
出典データセット
uspto-grants-2013_10
特許番号
US08557849B2

関連ノート

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