1,2-Dichloroethane → (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-5-nitrobenzoxazole

HRID 1821375Notes

Reaction equation

HRID 1821375 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=O)=[N:2]1.[NH2:21][C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1O.O.ON1C2C=CC=CC=2N=N1.C(Cl)CCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C.CCCCCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]2[O:16][C:23]3[CH:24]=[CH:25][C:26]([N+:28]([O-:30])=[O:29])=[CH:27][C:22]=3[N:21]=2)=[N:2]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 27960291-Hydroxybenzotriazole hydrateHCID 36133892-Amino-4-NitrophenolHCID 57586985(E)-2-[2-(1H-indazol-3-yl)vinyl]benzoic acid

Product 1

HCID 68999187(E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}-5-nitrobenzoxazoleYield 15%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

In a similar manner to Example 28, (E)-2-[2-(1H-indazol-3-yl)vinyl]benzoic acid (0.30 g, 1.1 mmol) obtained in Step 1 of Example 47, 2-amino-4-nitrophenol (0.19 g, 1.3 mmol), 1-hydroxybenzotriazole monohydrate (52 mg, 0.34 mmol), EDC (0.24 g, 1.3 mmol) and THF/DMF (2/1, 4.5 mL) were reacted. Then, in a similar manner to Step 2 of Example 150, the reaction mixture was treated with p-toluenesulfonic acid monohydrate (0.39 mg, 2.3 mmol) and xylene (10 mL) to obtain Compound 184 (63 mg, 14%).

Sources & evidence

ORD record
ord-7a19398636d94c07bd5e36a0772fa5d0
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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