HCID 58121056, compound → HCID 10377040, compound

HRID 1186688Notes

Reaction equation

HRID 1186688 reaction equation
[OH:1][NH:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOC(C)=O.CO.[Pd]>[OH:1][NH:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 1

HCID 58121056HCID 58121056, compound

Product 1

HCID 10377040HCID 10377040, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
21 °C

Procedure

A solution of N-hydroxy-2-(phenylethynyl)benzamide 37 (40 mg, 0.169 mmol) in EtOAc (1533 μL) and MeOH (153 pit) was degassed under vacuum and put under N2 atmosphere (3 cycles). Then a suspension of Pd/C (17.94 g, 0.017 mmol) in EtOAc (1 mL) was added and the resulting suspension was degassed and put under H2 atmosphere (3 cycles) and the resulting black suspension was stirred at 21° C. for 2 h. The reaction mixture was filtered through Celite®. The filtrate was concentrated in vacuo then crystallized from a mixture of Et2O and hexane to afford title compound 38 (25 mgs, 62% yield) as a white solid. 1H NMR: (DMSO-d6) δ (ppm): 10.90 (s, 1H), 9.10 (s, 1H), 7.37-7.22 (m, 8H), 7.18 (t, J=7.2 Hz, 1H), 2.93 (dt, J=9.8, 6.3 Hz, 2H), 2.84 (dt, J=9.7, 5.7 Hz, 2H). LRMS (ESI): (calc.) 241.29 (found) 242.22 (MH)+

Workup

  1. additionwas added
  2. customthe resulting suspension was degassed
  3. filtrationThe reaction mixture was filtered through Celite®
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthen crystallized from a mixture of Et2O and hexane

Sources & evidence

ORD record
ord-38c3eeca900d445ca8faa37a0511f542
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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