Thiophosgene → 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl isothiocyanate

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](Cl)(Cl)=[S:22]>>[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]([N:18]=[C:21]=[S:22])[CH:17]=1)=[CH:5]2

Participants

Reactant 2

HCID 10040Thiophosgene

HCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine2×

Product 1

HCID 225684385-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenyl isothiocyanate

Procedure

The product from Example 3, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine (5.48 g, 20 mmol) was reacted with thiophosgene (1.9 mL, 25 mmol) according to the procedure for Example 26, Step A to give the product as a greenish tan solid (5.40 g).

Sources & evidence

ORD record: ord-dc5cf2e30cef4cf492296d8aa530e53a
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06858739B2

Reaction notes

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