Dimethyl Sulfoxide → HCID 11559623, compound

HRID 1836615Notes

Reaction equation

HRID 1836615 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH:17]=[C:16]2[C@H:32]1[CH2:34][C@H:33]1[CH2:35][OH:36])#[N:12].C(N(CC)CC)C>ClCCl>[C:11]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH:17]=[C:16]2[C@H:32]1[CH2:34][C@H:33]1[CH:35]=[O:36])#[N:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 11646316HCID 11646316, compound

Product 1

HCID 11559623HCID 11559623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a −78° C. solution of oxalyl chloride (52 μL, 0.60 mmol) in anhydrous dichloromethane (20 ml) was added dimethylsulfoxide (50 μL, 0.70 mmol) dropwise. After stirring 10 min, a solution of cis-2-[5-Cyano-1-(p-toluenesulfonyl)indol-3-yl]cyclopropanemethanol (129 mg, 0.35 mmol) in dichloromethane (5 ml) was added dropwise. After stirring 20 min at −78° C., triethylamine (294 □L, 2.10 mmol) was added dropwise. The reaction was stirred for 5 min at −78° C. and then allowed to warm to room temperature. The reaction was washed with water (2×5 ml), dried with anhydrous magnesium sulfate and the solvent was evaporated to give the crude cis-2-[5-Cyano-1-(p-toluenesulfonyl)indol-3-yl]cyclopropanecarboxaldehyde.

Workup

  1. stirringAfter stirring 20 min at −78° C.
  2. stirringThe reaction was stirred for 5 min at −78° C.
  3. washThe reaction was washed with water (2×5 ml)
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-04221c773b8f4f37a58eaf463810d66b
Source dataset
uspto-grants-2004_08
Patent number
US06777437B2

Reaction notes

Loading…