Methanol → HCID 25207188, compound

HRID 1510334Notes

Reaction equation

HRID 1510334 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:26][P:27](=[O:34])([O:31]CC)[O:28]CC)[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22](=[O:25])[NH:23][CH3:24])[CH2:17][CH2:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C[Si](Br)(C)C.CO>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:26][P:27](=[O:28])([OH:34])[OH:31])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22](=[O:25])[NH:23][CH3:24])[CH2:17][CH2:16]3)(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 76113BromotrimethylsilaneHCID 59446523HCID 59446523, compound

Product 1

HCID 25207188HCID 25207188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.2 g diethyl {[(3,5-dichloro-phenylsulphonyl)-(1-methylcarbamoyl-2,3-dihydro-1H-indol-5-yl)-amino]-methyl}-phosphonate are dissolved in 30 ml dichloromethane. 1.2 ml of trimethylsilylbromide are added with stirring. Then the mixture is refluxed for 2 hours and after cooling to ambient temperature combined with 30 ml of methanol. The mixture is stirred for 1 hour, the solvents are eliminated in vacuo, another 30 ml of methanol are added and the mixture is stirred for a further 10 minutes. Then the solvent is eliminated in vacuo and the residue is dried in vacuo at 80° C. Then it is extracted from diethyl ether, the solid is suction filtered and dried in vacuo.

Workup

  1. temperatureThen the mixture is refluxed for 2 hours
  2. stirringThe mixture is stirred for 1 hour
  3. stirringthe mixture is stirred for a further 10 minutes
  4. customthe residue is dried in vacuo at 80° C
  5. extractionThen it is extracted from diethyl ether
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3d417a499b6a46c2b2281ecc6e9e99cd
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

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