Sodium hydride → HCID 45273621, compound

HRID 1631502Notes

Reaction equation

HRID 1631502 reaction equation
[H-].[Na+].C[O:4][C:5](=[O:17])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH3:16].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][C:20]=1[C:29]#[N:30]>C1COCC1.C1COCC1.CN(C=O)C>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:7]([CH2:6][C:5]([OH:4])=[O:17])=[C:8]2[CH3:16])(=[O:26])=[O:27])=[CH:21][C:20]=1[C:29]#[N:30]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 180728534-Chloro-3-cyanobenzenesulfonyl chlorideHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

Product 1

HCID 45273621HCID 45273621, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, ice-cooled (0° C.) suspension of sodium hydride (15.8 mg of a 60% dispersion in mineral oil, 0.411 mmol) in dry THF (2 ml) under an inert atmosphere of Argon is added dropwise (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester ((0.06 g, 0.294 mmol) in THF/DMF (4 ml of a 3:1 mixture). The reaction mixture is stirred at 0° C. for 45 minutes and then treated with 4-chloro-3-cyano-benzenesulfonyl chloride (97.1 mg, 0.411 mmol) in dry THF (3 ml). Stirring continued at 0° C. for 15 minutes and then the reaction mixture is poured onto water (30 ml) and extracted with ethyl acetate (100 ml). The organic portion is separated and washed brine (50 ml), dried (MgSO4) and concentrated in vacuo. The resulting crude is purified by chromatography on silica eluting with iso-hexane/ethyl acetate (0%-20% ethyl acetate) to yield the titled product. (MH+ 404)

Workup

  1. temperatureTo a stirred, ice-cooled
  2. stirringStirring
  3. waitcontinued at 0° C. for 15 minutes
  4. additionthe reaction mixture is poured onto water (30 ml)
  5. extractionextracted with ethyl acetate (100 ml)
  6. customThe organic portion is separated
  7. washwashed brine (50 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe resulting crude is purified by chromatography on silica eluting with iso-hexane/ethyl acetate (0%-20% ethyl acetate)

Sources & evidence

ORD record
ord-bbd7e5ccb9784ea3ae5be1b30bb3dc44
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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