Triphenylphosphine → N-(7-ethoxy-5,8-dihydronaphthalen-1-yl)-5-[4-(trifluoromethyl)phenyl]-1,3-oxazol-2-amine

HRID 600773

反応式

HRID 600773 の反応式
[CH2:1]([O:3][C:4]1[CH2:5][C:6]2[C:11]([CH2:12][CH:13]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[N:14]=[C:15]=S)[CH3:2].[N:17]([CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)=[O:22])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[CH2:1]([O:3][C:4]1[CH2:5][C:6]2[C:7]([NH:14][C:15]3[O:22][C:21]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=4)=[CH:20][N:17]=3)=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:12][CH:13]=1)[CH3:2]

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 53416493HCID 53416493、化合物HCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene

生成物 1

HCID 67229299N-(7-ethoxy-5,8-dihydronaphthalen-1-yl)-5-[4-(trifluoromethyl)phenyl]-1,3-oxazol-2-amine収率 22%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

A solution of the product of Example 1F (398 mg, 1.72 mmol), the product of Example 1G (473 mg, 2.07 mmol), and triphenyl phosphine (542 mg, 2.07 mmol) in dioxane (9 mL) was heated at 85° C. for 30 min. The solution was cooled to room temperature and evaporated in vacuo. The residue was chromatographed on silica gel, eluting with 25% ethyl acetate-hexane to afford the title compound as a yellow solid (150 mg, 22%). 1H NMR (DMSO-d6) δ 9.38 (s, 1H), 7.76 (m, 4H), 7.65 (d, 1H, J=8.5 Hz), 7.62 (s, 1H), 7.18 (t, 1H, J=8.2 Hz), 6.97 (d, 1H, J=8.4 Hz), 4.85 (m, 1H), 3.79 (q, 2H, J=6.7 Hz), 3.49 (m, 2H), 3.36 (m, 2H), 1.26 (t, 3H, J=6.8 Hz); MS (ESI+) m/z 401 (M+H)+.

後処理

  1. customevaporated in vacuo
  2. customThe residue was chromatographed on silica gel
  3. washeluting with 25% ethyl acetate-hexane

出典と根拠

ORDレコード
ord-b41cf446029949bbb8ffd8e5c20401fe
出典データセット
uspto-grants-2011_03
特許番号
US07902236B2

関連ノート

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