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

HRID 1631501Notes

Reaction equation

HRID 1631501 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:29])[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]([F:25])=[C:21]([O:26][CH3:27])[CH:20]=2)(=[O:18])=[O:17])[C:8]=1[CH3:28]>C1COCC1.O.C(Cl)Cl>[F: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:29])=[O:4])=[C:8]2[CH3:28])(=[O:17])=[O:18])=[CH:20][C:21]=1[O:26][CH3:27]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67219666[1-(4-Fluoro-3-methoxy-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

Product 1

HCID 45268524[1-(4-Fluoro-3-methoxy-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

Reagents, catalysts & solvents 2

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

Procedure

1 M Lithium hydroxide (119 μl) is added dropwise to a cooled (0° C.) solution of [1-(4-fluoro-3-methoxy-benzenesulfonyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (0.044 g, 0.119 mmol) in THF/water (4 ml of a 1:1 mixture). After stirring at room temperature for 4 hours, the reaction mixture is diluted with DCM. The resulting mixture is passed through a phase separation cartridge and the aqueous portion is acidified to pH 1-3 with 1M HCl. This portion is extracted with DCM and the organic extracts are combined and concentrated in vacuo to yield the titled compound as a pale yellow solid. (MH+ 379)

Workup

  1. customThe resulting mixture is passed through a phase separation cartridge
  2. extractionThis portion is extracted with DCM
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eba5dd9475164b3681eb0fcf032fe45c
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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