Bromomethyl 4-methoxyphenyl ketone → HCID 21907517, compound

HRID 1247463Notes

Reaction equation

HRID 1247463 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[C:6]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH2:20])=[S:19])=[CH:13][CH:12]=3)[CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3]1.Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)=O>C(O)C>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]2[N:20]=[C:18]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([C:6]4[CH:7]=[CH:8][CH:9]=[C:10]5[C:5]=4[CH2:4][NH:3][C:2]5=[O:1])=[CH:16][CH:15]=3)[S:19][CH:22]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 21907521HCID 21907521, compound

Product 1

HCID 21907517HCID 21907517, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of Example 125A (90 mg, 0.32 mmol) and 2-bromo-1-(4-methoxy-phenyl)ethanone (73 mg, 0.32 mmol) in ethanol (3 mL) was stirred at reflux for 2 hours, cooled to room temperature, and filtered. The filter cake was washed with ethanol and dichloromethane and dried to give 118 mg (90% yield) of the desired product as the hydrobromide salt. 1H NMR (300 MHz, DMSO-d6) δ 3.80 (s, 3H); 4.55 (s, 2H); 7.01 (d, J=8.81 Hz, 2H); 7.21 (s, 1H); 7.58–7.64 (m, 3H); 7.66–7.69 (m, 2H); 7.86 (dd, J=8.81, 7.12 Hz, 4H); 8.67 (s, 1H); 10.43 (s, 1H); MS (ESI(+)) m/e 414 (M+H)+.

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationfiltered
  3. washThe filter cake was washed with ethanol and dichloromethane
  4. customdried

Sources & evidence

ORD record
ord-75fd5fb4c95b4359a6f782de743175c9
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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