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 1258561노트

반응식

HRID 1258561 반응식
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

참가 물질

9

반응물 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

생성물 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-phenylmethanimine수율 72.8%

시약·촉매·용매 4

HCID 83717Copper iodide촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-549e6e5a003f43498cbb96299d7ff1c5
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466176B2

반응 노트

불러오는 중…