Hydrochloric Acid → HCID 69058556, compound

HRID 730416Notes

Reaction equation

[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[CH:9][C:10]=2[CH3:12])[N:5]([CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15]2)[C:4]=1/[CH:23]=[CH:24]/[C:25]([O:27]CC)=[O:26])#[N:2].[OH-].[Na+].O.Cl>C(O)C.O1CCCC1>[C:1]([C:3]1[C:11]2[C:6](=[N:7][C:8]([CH3:13])=[CH:9][C:10]=2[CH3:12])[N:5]([CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15]2)[C:4]=1/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26])#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl (2E)-3-[3-cyano-1-(indan-1-yl)-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl]acrylate (5.54 g) was dissolved in ethanol-tetrahydrofuran (1 : 1, v/v) (60 ml) and a 2 N aqueous sodium hydroxide solution (14.4 ml) was added thereto at 50° C. After agitating the mixture at 50° C. for 40 minutes, the reaction solution was poured into water (300 ml), and concentrated hydrochloric acid was added thereto to adjust the pH to 3 to 4. The resultant mixture was extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). After the organic layer was washed with water and dried (over anhydrous magnesium sulfate), the solvent was distilled off under reduced pressure and the crystal was collected by filtration to give (2E)-3-[3-cyano-1-(indan-1-yl)-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-2-yl]acrylic acid (4.55 g, 89%).

Workup

customat 50° C
additionwas added
extractionThe resultant mixture was extracted with ethyl acetate-tetrahydrofuran (3:1
washAfter the organic layer was washed with water
dry with materialdried (over anhydrous magnesium sulfate)
distillationthe solvent was distilled off under reduced pressure
filtrationthe crystal was collected by filtration

Sources & evidence

ORD record: ord-4ea236dbb4684462bc93e6bd3779f49c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582651B2

Reaction notes

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