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

HRID 649933Notes

Reaction equation

HRID 649933 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:3]=1[NH:4][C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[C:14](OCC)=O.[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C1(OC)C=CC=CC=1>[Ti](Cl)(Cl)(Cl)Cl>[Br:23][C:20]1[CH:21]=[CH:22][C:2]2[N:1]=[C:14]([N:28]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]3)[C:6]3[C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[S:9][C:5]=3[NH:4][C:3]=2[CH:19]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 531671-MethylpiperazineHCID 18422313Ethyl 2-(2-amino-5-bromoanilino)benzo[b]thiophene-3-carboxylate

Product 1

HCID 184223798-bromo-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 2-(2-amino-5-bromoanilino)benzo[b]thiophene-3-carboxylate, 1-methylpiperazine, anisole and titanium tetrachloride, 8-bromo-12-(4-methylpiperazin-1-yl)-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine is obtained.

Sources & evidence

ORD record
ord-6926d88b91d84564a8526c7c797d78fb
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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