HCID 57695507, compound → HCID 135987524, compound

HRID 2079851Notes

Reaction equation

HRID 2079851 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]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)=[CH:11][C:10]=1[C:33]1[N:37]([CH2:38][CH2:39][CH2:40][O:41][CH3:42])[N:36]=[N:35][N:34]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:42][O:41][CH2:40][CH2:39][CH2:38][N:37]1[C:33]([C:10]2[CH:11]=[C:12]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=3)[C:13]([OH:15])=[CH:14][C:9]=2[OH:8])=[N:34][N:35]=[N:36]1

Participants

5

Reactant 2

HCID 57695507HCID 57695507, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135987524HCID 135987524, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

5% Pd/C was wetted carefully with MeOH under N2, then 5-(4,6-bis-benzyloxy-3′-trifluoromethyl-biphenyl-3-yl)-1-(3-methoxy-propyl)-1H-tetrazole (90 mg, 0.16 mmol) solution in methanol was added. The reaction system was vacuumed and filled with hydrogen three times. The reaction was stirred under hydrogen at r.t. overnight. After filtering the catalyst over celite, the filtrate was concentrated to give 5-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-3′-trifluoromethyl-biphenyl-2,4-diol (50 mg, 82%). M.p.: 144-182° C.; 400 MHz 1H NMR (CDCl3) δ: 10.82 (s, 1H), 7.62 (s, 1H), 7.72-7.58 (m, 4H), 6.76 (s, 1H), 5.70 (s, 1H), 4.74 (t, J=7.6 Hz, 2H), 3.41 (t, J=6.8 Hz, 2H), 3.10 (s, 3H), 2.31-2.23 (m, 2H); LCMS: 395 [M+H].

Workup

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

Sources & evidence

ORD record
ord-9469e57995464689bfb3903a9538fe2e
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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