Sodium Chloride → 4-(5-(4-ethoxy-3-nitrophenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-ol
Reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.O[N:38]=[C:39]([C:41]1[C:42]2[CH2:43][CH2:44][CH:45]([OH:50])[C:46]=2[CH:47]=[CH:48][CH:49]=1)[NH2:40].[Na+].[Cl-]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]2[O:10][N:40]=[C:39]([C:41]3[CH:49]=[CH:48][CH:47]=[C:46]4[C:42]=3[CH2:43][CH2:44][CH:45]4[OH:50])[N:38]=2)=[CH:6][C:5]=1[N+:13]([O-:15])=[O:14])[CH3:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
In a microwave vial, a stirring solution of 4-ethoxy-3-nitrobenzoic acid (200 mg, 0.947 mmol) in DMF was treated with HOBt (167 mg, 1.231 mmol) and EDCI (236 mg, 1.231 mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of N′,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide (200 mg, 1.04 mmol). The reaction was stirred for additional 30 min at room temperature and then heated to 130° C. for 35 min in the initiator. The reaction was diluted using a saturated solution of NaCl and extracted with EtOAc (80 ml×3). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (9:1) to offer the product as pale yellow solid in 40% yield (150 mg).
Workup
- stirringThe reaction was stirred for additional 30 min at room temperature
- additionThe reaction was diluted
- extractionextracted with EtOAc (80 ml×3)
- dry with materialThe organic phase was dried over Na2SO4 anhydrous
- concentrationconcentrated under reduced pressure
- customThe product was purified by column chromatography
Sources & evidence
- ORD record
- ord-3f76f6a7b7b94865955e7c21a3738d50
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08530503B2
Reaction notes
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