Dimethyl Sulfoxide → HCID 22034359, compound

HRID 1792165Notes

Reaction equation

HRID 1792165 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([S:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH2:14][OH:15])[NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CS(C)=O.C(Cl)(=O)C([Cl:30])=O.C(N(CC)CC)C>C(Cl)Cl>[Cl:30][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[S:16][C:9]1[C:8]2[C:12](=[CH:13][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)[NH:11][C:10]=1[CH:14]=[O:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22034381HCID 22034381, compound

Product 1

HCID 22034359HCID 22034359, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of alcohol [3-(2-chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indol-2-yl]-methanol (75 mg) (prepared as described in Example 5) in CH2Cl2 (5 ml) was added to a solution of DMSO (0.2 ml) and oxalyl chloride (0.1 ml) that had been prepared at −78°. After 15 min triethylamine (0.45 ml) was added and the reaction was allowed to warm to 20° over 30 min. It was partitioned between EtOAc and water and the organic phase evaporated to give 3-(2-chloro-phenylsulfanyl)-6-methanesulfonyl-1H-indole-2-carboxaldehyde, 801, MS: 343 ([M+H]+).

Workup

  1. customhad been prepared at −78°
  2. temperatureto warm to 20° over 30 min
  3. customIt was partitioned between EtOAc and water
  4. customthe organic phase evaporated

Sources & evidence

ORD record
ord-2ae93c12a81d411fb6521d083ccbeaea
Source dataset
uspto-grants-2006_07
Patent number
US07074939B2

Reaction notes

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