3-Pyridyl isothiocyanate → 1-[5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-3-pyridin-3-yl-thiourea

HRID 25522Notes

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.[N:21]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[C:22]=[S:23]>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:22]([NH:21][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[S:23])[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 (0.277 g, 1.0 mmol) was mixed with 3-isothiocyanatopyridine (0.146 g, 1.07 mmol) in tetrahydrofuran (10 mL) and was heated briefly to 50° C. and then allowed to stand overnight at room temperature. The tetrahydrofuran was removed on the rotary evaporator to give a solid. The solid was triturated with hexanes/ethyl acetate, 1/1, v/v and was triturated a second time with hexanes/ethyl acetate, 4/1, v/v to give the product (0.309 g), mp 128-130° C.

Workup

customThe tetrahydrofuran was removed on the rotary evaporator
customto give a solid
customThe solid was triturated with hexanes/ethyl acetate, 1/1, v/v
customwas triturated a second time with hexanes/ethyl acetate, 4/1, v/v

Sources & evidence

ORD record: ord-f878aee7251846608a61d35112572504
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858739B2

Reaction notes

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