Lithium Hydroxide → 2-(1-(4-cyano-3-ethoxyphenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

HRID 1445641Notes

Reaction equation

HRID 1445641 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:31])[CH2:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[N:9]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([O:27][CH2:28][CH3:29])[CH:20]=2)(=[O:18])=[O:17])[C:8]=1[CH3:30]>C1COCC1.O.C(Cl)Cl>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([S:16]([N:9]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[C:7]([CH2:6][C:5]([OH:31])=[O:4])=[C:8]2[CH3:30])(=[O:18])=[O:17])=[CH:20][C:21]=1[O:27][CH2:28][CH3:29])#[N:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 672193091H-Pyrrolo[2,3-b]pyridine-3acetic acid,1-[(4-cyano-3-ethoxyphenyl)sulfonyl]-2-methyl-,methyl ester

Product 1

HCID 452727612-(1-(4-cyano-3-ethoxyphenylsulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

1M Lithium hydroxide (57 μl) is added dropwise to a cooled (0° C.) solution of [1-(4-cyano-3-ethoxy-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.024 g, 0.057 mmol) in THF/water (4 ml of a 1:1 mixture). After stirring at 0° C. for 10 minutes, the reaction mixture is stirred at room temperature for 2.5 hours and then diluted with DCM (4 ml). The resulting mixture is passed through a phase separation cartridge and the aqueous portion is acidified to pH 4 with 1M HCl. This portion is extracted with DCM (2×4 ml) and the organic extracts are combined, passed through a phase separation cartridge, and concentrated in vacuo. The resulting solid is dissolved in ethyl acetate (2 ml) and triturated with iso-hexane (7 ml) to yield the titled compound as a white solid. (MH+ 400)

Workup

  1. stirringthe reaction mixture is stirred at room temperature for 2.5 hours
  2. customThe resulting mixture is passed through a phase separation cartridge
  3. extractionThis portion is extracted with DCM (2×4 ml)
  4. custompassed through a phase separation cartridge
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting solid is dissolved in ethyl acetate (2 ml)
  7. customtriturated with iso-hexane (7 ml)

Sources & evidence

ORD record
ord-1ac15ca1219f4551b337c5b1e586ffd0
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

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