HCID 86644292, compound → HCID 25147517, compound

HRID 1807438Notes

Reaction equation

HRID 1807438 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:28][P:29](=[O:36])([O:33]CC)[O:30]CC)[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1>ClCCl.CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:28][P:29](=[O:30])([OH:33])[OH:36])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22]2[N:23]=[CH:24][CH:25]=[CH:26][N:27]=2)[CH2:17][CH2:16]3)(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 1

HCID 86644292HCID 86644292, compound

Product 1

HCID 25147517HCID 25147517, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

70 mg diethyl {[(3,5-dichloro-phenylsulphonyl)-(1-pyrimidin-2-yl-2,3-dihydro-1H-indol-5-yl)-amino]-methyl}-phosphonate are dissolved in 3 ml dichloromethane. Under argon 200 μl trimethylsilylbromide are added thereto and the mixture is refluxed for 2 hours. After cooling to ambient temperature 1 ml of methanol is added and the mixture is stirred for a further 1 hour. Then the solvents are eliminated in vacuo. The residue is taken up in 3 ml of methanol, stirred for 10 minutes and the solvent is eliminated in vacuo. The residue thus obtained is extracted from dichloromethane with 1% methanol. The solid is suction filtered and dried.

Workup

  1. additionUnder argon 200 μl trimethylsilylbromide are added
  2. temperaturethe mixture is refluxed for 2 hours
  3. additionis added
  4. stirringstirred for 10 minutes
  5. customThe residue thus obtained
  6. extractionis extracted from dichloromethane with 1% methanol
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-ab12f9d3f16a441f9875449ca4a379c1
Source dataset
uspto-grants-2013_01
Patent number
US08357689B2

Reaction notes

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