Lithium hydroxide, monohydrate → HCID 59467524, compound

HRID 655869Notes

Reaction equation

HRID 655869 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]#[N:18])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][CH:9]=2)=[O:5])C.O[Li].O>C1COCC1.O>[Br:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]#[N:18])[C:6]([C:4]([OH:5])=[O:3])=[CH:14]2

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 21223924HCID 21223924, compound

Product 1

HCID 59467524HCID 59467524, compoundYield 86%

Reagents, catalysts & solvents 1

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

Procedure

To a solution of 1.0 eq. of 5-Bromo-1-cyanomethyl-1H-indole-2-carboxylic acid ethyl ester (prepared according to U.S. Pat. No. 5,854,245) in a mixture of THF/H2O ((9/1) was added LiOH.H2O (1.0 eq.) and the reaction mixture stirred 6 h at RT, acidified to pH 2 and then partially concentrated until precipitation of the crude product which was filtered off and washed with Et2O and then dried to give the desired product as a beige solid (86%).

Workup

  1. concentrationpartially concentrated until precipitation of the crude product which
  2. filtrationwas filtered off
  3. washwashed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-b7f0eccdcaab4e2fad83c747e97dd42d
Source dataset
uspto-grants-2011_12
Patent number
US08071622B2

Reaction notes

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