Sodium Hydroxide → [1-(2-Chloro-4-methanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid

HRID 1260633Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

1M Aqueous NaOH (15 ml) is added to a stirring suspension of [1-(2-chloro-4-methanesulfonyl-benzyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester (2.6 g, 6.39 mmol) in 1:1 THF/MeOH (40 ml). After stirring at 45° C. for 1 hour, the reaction mixture is filtered to remove any undissolved material and is evaporated to dryness. The resulting solid is dissolved in water (30 ml) and acidified to pH 2-3 using concentrated HCl. The resulting suspension is collected by filtration and dried in vacuo at 50° C. to yield a solid which is purified by recrystallisation from IPA/water (1:3) to afford the titled product. (MH+ 393)

Workup

filtrationthe reaction mixture is filtered
customto remove any undissolved material
customis evaporated to dryness
dissolutionThe resulting solid is dissolved in water (30 ml)
filtrationThe resulting suspension is collected by filtration
customdried in vacuo at 50° C.
customto yield a solid which
customis purified by recrystallisation from IPA/water (1:3)

Sources & evidence

ORD record: ord-bfbb0c351b9145719e23bda80355d44e
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470848B2

Reaction notes

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