HCID 86690718, compound → HCID 86690719, compound

HRID 1473894Notes

Reaction equation

HRID 1473894 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[O:20])[O:12]3)[C:5]=12>CCOC(C)=O.[Pd]>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[O:20])[O:12]3)[C:5]=12

Participants

4

Reactant 1

HCID 86690718HCID 86690718, compound

Product 1

HCID 86690719HCID 86690719, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(imidazo[1,2-a]pyridin-8-ylmethylene)isobenzofuran-1(3H)-one (180 mg, 0.69 mmol) in EtOAc (12 mL) was added 10% Pd/C (110 mg). The mixture was stirred under a hydrogen balloon overnight. The catalyst was filtered off and the filtrate was concentrated and purified on silica gel with 10% MeOH/DCM as eluent to give 3-(imidazo[1,2-a]pyridin-8-ylmethyl)isobenzofuran-1(3H)-one (140 mg, 78%). 1H NMR (400 MHz, CD3OD) δ=8.37 (d, 1H), S 7.88 (s, 1H), 7.83 (d, 1H), 7.74-7.63 (m, 2H), 7.60-7.53 (m, 2H), δ 7.22 (d, 1H), 6.86 (t, 1H), 6.04 (dd, 1H), 3.76 (dd, 1H), 3.24 (dd, 1H). LRMS (M+H+) m/z 265.1

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. custompurified on silica gel with 10% MeOH/DCM as eluent

Sources & evidence

ORD record
ord-066717f22e6a4a86b25447a2f03d7282
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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