alpha-Bromo-o-fluorotoluene → HCID 71625272, compound

HRID 1831468Notes

Reaction equation

HRID 1831468 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.CCN(C(C)C)C(C)C.[F:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Br>CS(C)=O.C(#N)C>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][CH2:32][C:31]3[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=3[F:29])=[N:6][C:5]=2[N:19]=1

Participants

6

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 81531DiisopropylethylamineHCID 178445911HCID 178445911, compound

Product 1

HCID 71625272HCID 71625272, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

The product from step (a) (20 mg, 67 μmol) was suspended in dimethyl sulphoxide (450 μL) and Hunig's base (13 μL, 74 μmol) was added. 2-Fluorobenzyl bromide (8.0 μL, 67 μmol) was quickly added to the stirred solution. The reaction was stirred for 60 minutes to give a homogeneous solution The crude solution was diluted to 1 mL with acetonitrile and chromatographed on a reverse phase column using a gradient (40–70% acetonitrile) to give the title compound as a white solid (17 mg, 61% yield).

Workup

  1. customto give a homogeneous solution The crude solution
  2. customchromatographed on a reverse phase column

Sources & evidence

ORD record
ord-adeb0f851f6c4fb2bb34c5db435a003f
Source dataset
uspto-grants-2006_06
Patent number
US07067657B2

Reaction notes

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