Lithium Hydroxide → HCID 68295463, compound

HRID 1912533Notes

Reaction equation

HRID 1912533 reaction equation
[C:1]([O:5][CH:6]([C:11]1[C:12]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO.O1CCCC1>[C:1]([O:5][CH:6]([C:11]1[C:12]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71209017HCID 71209017, compound

Product 1

HCID 68295463HCID 68295463, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of methyl 2-(tert-butoxy)-2-(1-(4-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (44 mg, 0.093 mmol) in methanol (0.5 mL) and tetrahydrofuran (THF) (0.500 mL) was treated with LiOH (0.278 mL, 0.556 mmol) and stirred at 60° C. for 18 hours. The reaction was concentrated and purified with reverse phase HPLC (20-100% MeCN/H2O-0.1% TFA) to afford 2-(tert-butoxy)-2-(1-(4-fluorobenzyl)-6-methyl-4-(p-tolyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (30.8 mg, 0.066 mmol, 71.4% yield) as white solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.69-7.56 (m, 1 H), 7.43-7.30 (m, 3 H), 7.29-7.25 (m, 2 H), 7.08-6.91 (m, 3 H), 6.24 (d, J=3.6 Hz, 1 H), 5.65-5.38 (m, 3 H), 2.77 (s, 3 H), 2.46 (s, 3 H), 0.94 (s, 9 H); LCMS (m/z) ES+=461 (M+1).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified with reverse phase HPLC (20-100% MeCN/H2O-0.1% TFA)

Sources & evidence

ORD record
ord-6c1ea84a252a483a816c06f30c4ca9c7
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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