Lithium hydroxide, monohydrate → N-(3-Methoxybenzyl)-5-(1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide

HRID 2108756Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[N:17](S(C3C=CC(C)=CC=3)(=O)=O)[CH:16]=2)[S:12][CH:11]=1)=[O:9].O[Li].O>C1COCC1.O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[CH2:6][NH:7][C:8]([C:10]1[CH:14]=[C:13]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[S:12][CH:11]=1)=[O:9]

Participants

Conditions

Temperature: 150 °C

Procedure

N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide (70 mg, 0.14 mmol) was dissolved in THF (4 mL) and LiOH hydrate (42 mg, 1 mmol) was added in water (1 mL). The reaction mixture was heated to 150° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc and the organic layer was washed with 10% citric acid, saturated sodium bicarbonate, and then dried over sodium sulfate and concentrated to an oil, which was purified by column chromatography on silica (50 to 100% EtOAc/hexanes) to give the product as a white solid 30 mg, 0.083 mmol, 59%. 1H NMR 500 MHz (DMSO-d6) 12.00 (1H, s), 8.88 (1H, t), 8.32 (2H, m), 8.01 (1H, s), 7.87 (1H, s), 7.83 (1H, s), 7.26 (2H, m), 6.92 (2H, m), 6.93 (2H, m), 6.82 (1H, d), 4.43 (2H, d), 3.70 (3H, s). MH+ 364.10

Workup

washthe organic layer was washed with 10% citric acid, saturated sodium bicarbonate
dry with materialdried over sodium sulfate
concentrationconcentrated to an oil, which
customwas purified by column chromatography on silica (50 to 100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-473755695469487fb08fad6797446551
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514448B2

Reaction notes

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