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

HRID 1821374Notes

Reaction equation

HRID 1821374 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]=[CH:26][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][CH:26]=[CH:27][C:22]=3[N:21]=2)=[N:2]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 58012-AminophenolHCID 521998p-Toluenesulfonic acid monohydrateHCID 27960291-Hydroxybenzotriazole hydrateHCID 57586985(E)-2-[2-(1H-indazol-3-yl)vinyl]benzoic acid

Product 1

HCID 69002269(E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}benzoxazoleYield 5.1%

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 (0.20 g, 0.76 mmol) obtained in Step 1 of Example 47, 2-aminophenol (91 mg, 0.83 mmol), 1-hydroxybenzotriazole monohydrate (35 mg, 0.23 mmol), EDC (0.16 mg, 0.83 mmol) and THF/DMF (2/1, 3.0 mL) were reacted. Then, in a similar manner to Step 2 of Example 150, the reaction mixture was treated with p-toluenesulfonic acid monohydrate (0.26 mg, 1.5 mmol) and xylene (5.0 mL) to obtain Compound 183 (13 mg, 5%).

Sources & evidence

ORD record
ord-aecf9f359a254d73abc84426f94ee57d
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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