8,5-Dichloro-5H-dibenzo[b,e][1,4]diazepine → 8-Chloro-11-(4-fluorobenzyl)-5H-dibenzo[b,e][1,4]diazepine

HRID 2109910Notes

Reaction equation

HRID 2109910 reaction equation
[Cl-].[F:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Zn+])=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21](Cl)[C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[CH:18]=[N:17][C:16]=2[CH:27]=1>>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[NH:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[C:18]([CH2:7][C:6]3[CH:9]=[CH:10][C:3]([F:2])=[CH:4][CH:5]=3)=[N:17][C:16]=2[CH:27]=1

Participants

3

Reactant 2

HCID 574854318,5-Dichloro-5H-dibenzo[b,e][1,4]diazepineHCID 178505764HCID 178505764, compound

Product 1

HCID 1360292458-Chloro-11-(4-fluorobenzyl)-5H-dibenzo[b,e][1,4]diazepineYield 77.2%

Procedure

4-Fluorobenzylzinc chloride (0.8 ml, 0.5 M in THF, 0.4 mmol) and 8,5-dichloro-5H-dibenzo[b,e][1,4]diazepine (160FE64) (53 mg, 0.2 mmol) were reacted according GP10 to give 52 mg of the title compound (160FE59). MS (ESI) 337 (MH+). Purity for MH+ (UV/MS) 90/90.

Sources & evidence

ORD record
ord-7b2674bb18704bfcb9123a4df8bb2eb4
Source dataset
uspto-grants-2009_04
Patent number
US07517871B2

Reaction notes

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