HCID 60166734, compound → HCID 60166735, compound

HRID 1485828Notes

Reaction equation

HRID 1485828 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1)C1C=CC=CC=1>[Pd].CO.C(Cl)Cl>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25])=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=1

Participants

5

Reactant 1

HCID 60166734HCID 60166734, compound

Product 1

HCID 60166735HCID 60166735, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Palladium on carbon (10%, 5 mg) was added to 8a (120 mg, 0.35 mmol) in degassed MeOH (3.5 mL) and the solution was placed under an atmosphere of H2. After 12 h, the solution was diluted with DCM and filtered through Celite. The eluent was concentrated to afford a yellow solid, which was purified by column chromatography (SiO2, 100:5, DCM:MeOH) to afford phenol 9a (64 mg, 0.25 mmol, 79%) as a pale yellow amorphous solid. 1H NMR (400 MHz, CDCl3) δ 7.25-7.14 (m, 5H), 7.11-7.05 (m, 1H), 6.90 (d, J=8.3 Hz, 1H), 6.64 (d, J=8.3 Hz, 1H), 6.59 (d, J=2.5 Hz, 1H), 5.61 (t, J=5.5 Hz, 1H), 3.12-3.02 (m, 2H), 2.55 (t, J=7.1 Hz, 2H), 1.66 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 171.2, 155.2, 143.4, 141.6, 130.8, 129.1, 128.4, 127.2, 127.2, 117.4, 115.0, 41.1, 31.8, 23.2; HRMS m/z: [M+Na+] for C16H17NO2Na, calcd, 278.1151. found, 278.1155.

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe eluent was concentrated
  3. customto afford a yellow solid, which
  4. customwas purified by column chromatography (SiO2, 100:5, DCM:MeOH)

Sources & evidence

ORD record
ord-e871066b8aa641be9f4fe7e9fc807739
Source dataset
uspto-grants-2016_08
Patent number
US09422320B2

Reaction notes

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