Dimethyl Sulfoxide → HCID 136367318, compound

HRID 2234105Notes

Reaction equation

HRID 2234105 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][OH:28])[CH:25]=2)[CH:20]=[C:19]1[C:29]1[CH:34]=[C:33]([C:35]2[CH:40]=[C:39]([CH3:41])[C:38]([OH:42])=[C:37]([CH3:43])[CH:36]=2)[N:32]=[N:31][C:30]=1[O:44][CH3:45])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH:27]=[O:28])[CH:25]=2)[CH:20]=[C:19]1[C:29]1[CH:34]=[C:33]([C:35]2[CH:36]=[C:37]([CH3:43])[C:38]([OH:42])=[C:39]([CH3:41])[CH:40]=2)[N:32]=[N:31][C:30]=1[O:44][CH3:45])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 136367317HCID 136367317, compound

Product 1

HCID 136367318HCID 136367318, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A dry flask is charged with 0.399 mL oxalyl chloride and 69 mL dichloromethane. After cooling to −78° C. 0.304 mL DMSO is added dropwise. After stirring for 15 minutes at this temperature, 2.04 g (6-hydroxymethyl-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester in 46 mL dichloromethane are slowly added by syringe. After stirring for 60 minutes at −78° C. 2.98 mL triethylamine is added. The reaction mixture is stirred for 60 minutes at −78° C., allowed to warm to 0° C. and quenched by addition of sat. aq. NH4Cl-solution. The reaction mixture is diluted with dichloromethane, washed with sat. aq. NH4Cl-solution and brine, dried (MgSO4) and concentrated in vacuo. 1.96 g (97%) crude 6-formyl-2-[6-(4-hydroxy-3,5-dimethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester are obtained.

Workup

  1. additionare slowly added by syringe
  2. stirringThe reaction mixture is stirred for 60 minutes at −78° C.
  3. temperatureto warm to 0° C.
  4. customquenched by addition of sat. aq. NH4Cl-solution
  5. additionThe reaction mixture is diluted with dichloromethane
  6. washwashed with sat. aq. NH4Cl-solution and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18d814863cb24ce18868910b21d398ad
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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