HCID 58052505, compound → HCID 54576008, compound

HRID 2190156Notes

Reaction equation

HRID 2190156 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH3:17])=[C:11]([CH:14]=[CH2:15])[CH:12]=2)[O:7][C:6]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:4]>[OH-].[OH-].[Pd+2].C(OCC)(=O)C.CO>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH3:17])=[C:11]([CH2:14][CH3:15])[CH:12]=2)[O:7][C:6]=1[C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1)=[O:4]

Participants

4

Reactant 1

HCID 58052505HCID 58052505, compound

Product 1

HCID 54576008HCID 54576008, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To 2-(4-Fluoro-phenyl)-6-(methanesulfonyl-methyl-amino)-5-vinyl-furo[2,3-b]pyridine-3-carboxylic acid methylamide (11 mg, 0.027 mmol) was added 8 mg of 20% Pd(OH)2/C and ethyl acetate/methanol 5/1 (5 ml). The reaction flask was evacuated and filled with hydrogen gas from a balloon. After LCMS indicated conversion to product, the reaction mixture was filtered, evaporated to dryness and purified by HPLC to afford 5-Ethyl-2-(4-fluoro-phenyl)-6-(methanesulfonyl-methyl-amino)-furo[2,3-b]pyridine-3-carboxylic acid methylamide. MS (ESI) m/z 406.3 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.18 (s, 1H), 7.96-7.92 (m, 2H), 7.25-7.20 (m, 2H), 5.79 (br s, 1H), 3.32 (s, 3H), 3.19 (s, 3H), 2.99-2.98 (d, 3H), 2.96-2.91 (q, 2H), 1.33-1.29 (t, 3H).

Workup

  1. customThe reaction flask was evacuated
  2. additionfilled with hydrogen gas from a balloon
  3. filtrationthe reaction mixture was filtered
  4. customevaporated to dryness
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-c88bf96d26a54f9db6d040761fa1045f
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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