Sodium hydride → HCID 23550270, compound

HRID 1861021Notes

Reaction equation

HRID 1861021 reaction equation
[F:1][C:2]1[C:3]([C:12](I)=[CH:13][C:14](=O)[C:15]2[NH:16][CH:17]=[C:18]([CH3:21])[C:19]=2[CH3:20])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[H-].[Na+].[C:26]([O:30][C:31](=[O:36])[NH:32][CH2:33][CH2:34][SH:35])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([O:30][C:31](=[O:36])[NH:32][CH2:33][CH2:34][S:35][C:12]1[CH:13]=[C:14]([C:15]2[NH:16][CH:17]=[C:18]([CH3:21])[C:19]=2[CH3:20])[C:5]2[C:6](=[O:11])[NH:7][C:8]3[C:4]=2[C:3]=1[C:2]([F:1])=[CH:10][CH:9]=3)([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 86586104HCID 86586104, compound

Product 1

HCID 23550270HCID 23550270, compound

Procedure

To a suspension of 5-fluoro-4-[1-iodo-3-oxo-3-(3,4-dimethyl-1H-pyrrol-2-yl)-propenyl]-1,3-dihydro-indol-2-one (from Example 48 above) (1.58 g, 4.0 mmol) in tert-butyl-N-(2-mercaptoethyl)-carbamate (Aldrich, 8 mL) was added NaH (Aldrich, 95%, 0.3 g, 11.8 mmol) in portions at room temperature. After stirring at room temperature for 30 minutes, the reaction mixture was heated to 120° C. for 3 hours. The reaction was quenched by adding brine and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. Purification of the residue by flash chromatography (silica gel, 4:1 hexanes/ethyl acetate) afforded [2-[6-fluoro-2-oxo-3-(3,4-dimethyl-1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylsulfanyl]-ethyl]-carbamic acid tert-butyl ester as an orange oil. (Yield 66 mg, 31%).

Workup

  1. temperaturethe reaction mixture was heated to 120° C. for 3 hours
  2. customThe reaction was quenched
  3. additionby adding brine and ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography (silica gel, 4:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-2e57d3720a3c4a1d967ad24b89be2ced
Source dataset
uspto-grants-2003_03
Patent number
US06531598B1

Reaction notes

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