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

HRID 600773
Notes
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Reaction equation

HRID 600773 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 534164932-Azido-1-[4-(trifluoromethyl)phenyl]ethanoneHCID 866096122-Ethoxy-8-isothiocyanato-1,4-dihydronaphthalene

Product 1

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

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-b41cf446029949bbb8ffd8e5c20401fe
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902236B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes