Sodium hydride → HCID 11618107, compound

HRID 1631479Notes

Reaction equation

HRID 1631479 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[Cl:14])[N:7]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:6]=1[CH3:26].COC(=O)CC1C2C(=NC=CC=2Cl)NC=1C.[H-].[Na+].CS(C1C=CC(CBr)=CC=1)(=O)=O>CN(C=O)C.O>[Cl:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]2[N:7]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[C:6]([CH3:26])=[C:5]([CH2:4][C:3]([OH:27])=[O:2])[C:13]=12

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 27335814-(Methylsulfonyl)benzyl BromideHCID 67219047HCID 67219047, compoundHCID 67219495HCID 67219495, compound

Product 1

HCID 11618107HCID 11618107, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

[4-Chloro-1-(4-methanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester: To a cooled (0° C.) stirred solution of (4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (0.1 g, 0.42 mmol) in dry DMF (2.5 ml) is added sodium hydride (0.019 g of a 60% dispersion in mineral oil, 0.47 mmol). After stirring at room temperature for 5 hours, the reaction mixture is re-cooled to 0° C. and treated with 4-methylsulfonylbenzyl bromide (0.105 g, 0.42 mmol). The resulting mixture is stirred and allowed to warm to room temperature overnight. The reaction mixture is diluted with water (3 ml) and extracted with ether (3×15 ml). The organic portions are combined, washed with water, dried (Na2SO4) and concentrated in vacuo. The resulting crude residue is loaded on a pre-packed Isolute™ silica column and eluted with iso-hexane:ethyl acetate (1:8) to yield the titled compound as a white powder. (MH+ 407).

Workup

  1. temperaturethe reaction mixture is re-cooled to 0° C.
  2. stirringThe resulting mixture is stirred
  3. temperatureto warm to room temperature overnight
  4. extractionextracted with ether (3×15 ml)
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. washeluted with iso-hexane:ethyl acetate (1:8)

Sources & evidence

ORD record
ord-8548c3bd6a354eb98d2a750442d97894
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

Loading…