3-Fluorobenzyl bromide → HCID 59161237, compound

HRID 545524Notes

Reaction equation

HRID 545524 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH2:7][CH:8]([NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[CH2:9][CH2:10][C:11]=3[NH:12]2)=[CH:4][C:3]=1[C:21]#[N:22].ClC1C(C#N)=CC=C2C=1C1CC(NC(=O)C(C)C)CCC=1N2.[F:45][C:46]1[CH:47]=[C:48]([CH:51]=[CH:52][CH:53]=1)[CH2:49]Br>>[Cl:1][C:2]1[C:3]([C:21]#[N:22])=[CH:4][CH:5]=[C:13]2[C:14]=1[C:10]1[CH2:9][CH:8]([NH:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])[CH2:7][CH2:6][C:11]=1[N:12]2[CH2:49][C:48]1[CH:51]=[CH:52][CH:53]=[C:46]([F:45])[CH:47]=1

Participants

4

Reactant 3

HCID 680073-Fluorobenzyl bromideHCID 57431652HCID 57431652, compoundHCID 59161286HCID 59161286, compound

Product 1

HCID 59161237HCID 59161237, compoundYield 5%

Procedure

Prepare the title compound by essentially following the procedure as described in Example 96 with N-(7-chloro-6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide and N-(5-chloro-6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl)-isobutyramide (50:50 mixture—Preparation 17) and 3-fluorobenzyl bromide, to obtain a mixture of regioisomers. Separate the title compound from this mixture of regioisomers using silica gel chromatography (0-20% EtOAc/CHCl3), to afford the title compound in 5% yield. MS (ES): m/z 424 (M+1), 422 (M−1); HPLC (Method B): Rt=6.87 min, (97%).

Workup

  1. customto obtain
  2. additiona mixture of regioisomers
  3. customSeparate the title compound
  4. additionfrom this mixture of regioisomers

Sources & evidence

ORD record
ord-4a4882fa270847528080e8d1b8c687d9
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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