Lithium hydroxide, monohydrate → 3-Bromothieno[3,2-b]pyridine-2-carboxylic acid

HRID 57155Notes

Reaction equation

HRID 57155 reaction equation
C[O:2][C:3]([C:5]1[S:13][C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[Br:14])=[O:4].O[Li].O>C1COCC1.O>[Br:14][C:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[S:13][C:5]=1[C:3]([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57920438HCID 57920438, compound

Product 1

HCID 579204193-Bromothieno[3,2-b]pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

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

Procedure

To a solution of compound 145-E (4.94 g, 18.2 mmol) in 5:1 THF/H2O (200 mL) was added LiOH.H2O (0.797 g, 19.0 mmol). The reaction was stirred for 3 days then concentrated in vacuo, to which was added water (100 mL) and 1N HCl (19.0 mL), and the resultant precipitate was isolated by filtration. The solid was rinsed with water and dried under vacuum to afford compound 145-F as a tan-yellow solid (4.51 g, 96%). 1H-NMR (DMSO-d6): δ 7.62 (dd, 1H), 8.62 (dd, 1H), 8.86 (dd, 1H), 14.18 (br s, 1H); MS: m/z 257.9 (MH+).

Workup

  1. concentrationthen concentrated in vacuo, to which
  2. additionwas added water (100 mL) and 1N HCl (19.0 mL)

Sources & evidence

ORD record
ord-4f7e0127c7fd452192067d1af66a95c5
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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