Anisole → 3-bromo-8-fluoro-12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

HRID 649941Notes

Reaction equation

HRID 649941 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10](OCC)=O)=[C:8]([NH:15][C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[NH2:23])[S:7][C:6]=2[CH:24]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C1(OC)C=CC=CC=1>[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[C:10]([N:29]4[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]4)=[N:23][C:17]4[CH:18]=[CH:19][C:20]([F:22])=[CH:21][C:16]=4[NH:15][C:8]=3[S:7][C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 531671-MethylpiperazineHCID 18422173Ethyl 6-bromo-2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylate

Product 1

HCID 184223483-bromo-8-fluoro-12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

In the same manner as in Example 1 and using ethyl 6-bromo-2-(2-amino-5-fluoroanilino)benzo[b]thiophene-3-carboxylate (3.8 g), 1-methylpiperazine (16 ml), anisole (85 ml) and titanium tetrachloride (3.0 ml), 3-bromo-8-fluoro-12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine (1.16 g) was obtained.

Sources & evidence

ORD record
ord-7d1acb9f7400416c9c9f6e763beb667f
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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