Sodium methanesulfinate → HCID 52933354, compound

HRID 1423077Notes

Reaction equation

HRID 1423077 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12]([C:14]2[C:15]3[CH:16]=[CH:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21](Br)[CH:22]=2)=[O:13])[CH2:9][CH3:10])=[CH:4][CH:3]=1.[CH3:31][S:32]([O-:34])=[O:33].[Na+]>CS(C)=O.[I+].[Cu+]>[CH3:31][S:32]([C:2]1[N:7]=[CH:6][C:5]([C@@H:8]([NH:11][C:12]([C:14]2[C:15]3[CH:16]=[CH:17][N:18]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[C:19]=3[CH:20]=[C:21]([S:32]([CH3:31])(=[O:34])=[O:33])[CH:22]=2)=[O:13])[CH2:9][CH3:10])=[CH:4][CH:3]=1)(=[O:34])=[O:33]

Participants

5

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 86672837HCID 86672837, compound

Product 1

HCID 52933354HCID 52933354, compound

Reagents, catalysts & solvents 2

HCID 178505377HCID 178505377, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

A microwave tube is charged with 6-bromo-1-(4-fluorophenyl)-1H-indole-4-carboxylic acid [(S)-1-(6-bromopyridin-3-yl)-propyl]-amide (90.0 mg, 0.170 mmol, prepared as described in Example 5), copper (I) iodine (143 mg, 0.75 mmol) and sodium methanesulfinate (77 mg, 0.75 mmol) in DMSO (20 mL). The tube is capped and the solution is degassed with argon for 3 minutes. The mixture is warmed in a microwave reactor at 130° C. After 40 minutes, the reaction is diluted with saturated aqueous ammonium chloride (100 mL), saturated aqueous sodium bicarbonate (50 mL) and extracted with EtOAc. The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude mixture is purified by reversed-phase HPLC to afford the title compound.

Workup

  1. customThe tube is capped
  2. customthe solution is degassed with argon for 3 minutes
  3. additionthe reaction is diluted with saturated aqueous ammonium chloride (100 mL), saturated aqueous sodium bicarbonate (50 mL)
  4. extractionextracted with EtOAc
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude mixture is purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-68bcc666f61c4843870b645c6958305e
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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