Water → HCID 59508110, compound

HRID 1958642Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([O:20]C)=[O:19])=[CH:13][CH:12]=3)=[CH:7][CH:6]=[CH:5][N:4]=1.[OH-].[Li+].O>CO>[CH3:1][O:2][C:3]1[C:8]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=3)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of methyl 2-(2-methoxypyridin-3-yl)-1H-indole-5-carboxylate (1.0 g, 0.354 mmol) in methanol (100 ml) was added lithium hydroxide (0.30 g, 1.25 mmol) and water (10 ml). The reaction was heated overnight at 80° C. The reaction was not complete so more lithium hydroxide (0.10 g, 0.42 mmol) was added and heating was continued for 4 hours. The reaction was allowed to cool and stir at room temperature overnight. The reaction was concentrated to about 15 ml and 1 g citric acid dissolved in 10 ml of water was added. The solid was filtered, washed with water (25 ml) and dried under high vacuum at 50° C. The desired product was obtained as a white solid and used in the next reaction without any purification (0.9 g, 94%). 400 MHz 1H NMR (DMSO-d6) δ: 12.56 (bs, 1H), 11.69 (s, 1H), 8.30-8.12 (m, 3H), 7.75 (dd, J=1.6 Hz, 8.5 Hz, 1H), 7.50 (d, J=8.8 Hz, 1H), 7.24-7.09 (m, 2H), 4.06 (s, 3H). LCMS: 269 [M+H]

Workup

additionwas added
temperatureheating
temperatureto cool
concentrationThe reaction was concentrated to about 15 ml and 1 g citric acid
dissolutiondissolved in 10 ml of water
additionwas added
filtrationThe solid was filtered
washwashed with water (25 ml)
customdried under high vacuum at 50° C

Sources & evidence

ORD record: ord-0abda107332a477f924c42b2d840f401
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410144B2

Reaction notes

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