Ethyl Acetate → 3-{3-[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic acid

HRID 25494

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH2:18])[CH:17]=1)=[CH:5]2.[C:21]([C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[S:32])[CH:27]=[CH:28][CH:29]=1)([OH:23])=[O:22].C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH:18][C:31](=[S:32])[NH:30][C:26]3[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=3)[C:21]([OH:23])=[O:22])[CH:17]=1)=[CH:5]2

Participants

Conditions

Temperature: 50 °C

Procedure

The product from Example 3, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine, (0.274 g, 1.0 mmol) was mixed with 3-carboxyphenyl isothiocyanate (0.185 g, 1.0 mmol) in tetrahydrofuran (10 mL) and was heated briefly to 50° C. and then allowed to stand overnight at room temperature. The tetrahydrofuran was boiled off on the rotary evaporator (no vacuum) to give a solid. Ethyl acetate (10 mL) was added, and the mixture was allowed to stand overnight at room temperature. The insoluble material was collected by filtration, washed with ethyl acetate, and air-dried to give the product (0.379 g), mp 221-223° C.

Workup

customThe tetrahydrofuran was boiled off on the rotary evaporator (no vacuum)
customto give a solid
waitto stand overnight at room temperature
filtrationThe insoluble material was collected by filtration
washwashed with ethyl acetate
customair-dried

Sources & evidence

ORD record: ord-0ea489351c654338b1e2cfab35f4599c
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858739B2

Linked notes

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