HCID 57695533, compound → HCID 135987546, compound

HRID 2079860Notes

Reaction equation

HRID 2079860 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=2[O:32][CH3:33])=[CH:11][C:10]=1[C:34]1[N:38]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[N:37]=[N:36][N:35]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH:29]([C:27]1[CH:26]=[CH:25][C:24]([O:32][CH3:33])=[C:23]([C:12]2[C:13]([OH:15])=[CH:14][C:9]([OH:8])=[C:10]([C:34]3[N:38]([CH2:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[N:37]=[N:36][N:35]=3)[CH:11]=2)[CH:28]=1)([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 57695533HCID 57695533, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135987546HCID 135987546, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

5% Pd/C (30 mg) was wetted carefully with methanol under nitrogen in a 25 ml round flask, then a solution of 5-(4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-yl)-1-phenethyl-1H-tetrazole (100 mg, 0.16 mmol) in methanol (10 ml) was added. The reaction flask was vacuumed and filled with hydrogen three times. The reaction was then stiffed under hydrogen at r.t. overnight. After filtering the catalyst over celite, the filtrate was concentrated to give 5′-isopropyl-2′-methoxy-5-(1-phenethyl-1H-tetrazol-5-yl)-biphenyl-2,4-diol (44 mg, 63%). M.p.: 206-209° C.; 400 MHz 1H NMR (DMSO-d) δ: 10.22 (s, 1H), 9.64 (s, 1H), 7.19-7.08 (m, 4H), 7.02-6.97 (m, 3H), 6.94 (d, J=8.4 Hz, 1H), 6.75 (s, 1H), 6.61 (s, 1H), 4.55 (t, J=7.2 Hz, 2H), 3.66 (s, 3H), 3.11 (t, J=7.2 Hz, 2H), 2.90-2.81 (m, 1H), 1.20 (d, J=7.2 Hz, 6H); LCMS: 431 [M+H].

Workup

  1. filtrationAfter filtering the catalyst over celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1acc202080174214b716cc9dbe9fbc36
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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