Lithium hydroxide, monohydrate → HCID 59239688, compound

HRID 552262Notes

Reaction equation

HRID 552262 reaction equation
Br.[Br:2][C:3]1[CH:4]=[C:5]2[C:11]([C:12]3[N:13]=[C:14]([C:17]([O:19]CC)=[O:18])[S:15][CH:16]=3)=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1.O[Li].O>O.C1COCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:11]([C:12]3[N:13]=[C:14]([C:17]([OH:19])=[O:18])[S:15][CH:16]=3)=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67165382HCID 67165382, compound

Product 1

HCID 59239688HCID 59239688, compoundYield 82.6%

Reagents, catalysts & solvents 1

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

Procedure

To a stirred solution of ethyl 4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)thiazole-2-carboxylate hydrobromide (XXIII-a) (4.03 g, 9.30 mmol) in water:THF 1:1 (50 mL) was added LiOH·H2O (900 mg, 21.45 mmol) portionwise over 30 min. After stirring for 3 h, the reaction mixture was filtered to afford a yellow solid (2.49 g). The filtrate was then concentration to ˜20 mL by evaporation, and filtered again to afford a further 820 mg of yellow solid. The solids were combined to afford (XXIII-b) (3.31g, crude yield >100%). 1H NMR (400 MHz, D-6 DMSO) δ 7.76 (s, 1H), 8.03 (s, 1H), 7.73-7.78 (m, 3H), 8.32 (d, J=2.3 Hz, 1H), 8.74 (d, J=2.3 Hz, 1H), 12.09 (br s, 1H).

Workup

  1. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-82e466ef9cf94deab1711ea9b918ecdd
Source dataset
uspto-grants-2011_05
Patent number
US07951802B2

Reaction notes

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