Dimethyl Sulfoxide → HCID 22034359, compound

HRID 2218234Notes

Reaction equation

HRID 2218234 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 200 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 200 over 30 min
  3. customIt was partitioned between EtOAc and water
  4. customthe organic phase evaporated

Sources & evidence

ORD record
ord-c2799fc6678e4973979be42af24c464a
Source dataset
uspto-grants-2008_08
Patent number
US07410994B2

Reaction notes

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