Ethanol → HCID 57695507, compound

HRID 2079850Notes

Reaction equation

HRID 2079850 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](Br)=[CH:11][C:10]=1[C:24]1[N:28]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[N:27]=[N:26][N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:37]=[C:38](B(O)O)[CH:39]=[CH:40][CH:41]=1.C(O)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([C:35]([F:46])([F:45])[F:34])[CH:41]=2)=[CH:11][C:10]=1[C:24]1[N:28]([CH2:29][CH2:30][CH2:31][O:32][CH3:33])[N:27]=[N:26][N:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 57695508HCID 57695508, compound

Product 1

HCID 57695507HCID 57695507, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The mixture of 5-(2,4-bis-benzyloxy-5-bromo-phenyl)-1-(3-methoxy-propyl)-1H-tetrazole (110 mg, 0.22 mmol) and 3-trifluoromethylphenylboronic acid (83 mg, 0.44 mmol) was heated in a mixture of toluene (2 ml), ethanol (2 ml) and saturated sodium bicarbonate (2 ml) under nitrogen in the presence of a catalytic amount of Pd(PPh3)4 (20 mg) at 80° C. for 2-3 h. After the reaction was complete, the reaction mixture was extracted with ethyl acetate (15 ml×3), and the combined organics were washed with water and brine and dried over Na2SO4. After filtration and concentration, the residue was purified by flash chromatography on silica gel to provide 5-(4,6-bis-benzyloxy-3′-trifluoromethyl-biphenyl-3-yl)-1-(3-methoxy-propyl)-1H-tetrazole (90 mg, 72%). 400 MHz 1H NMR (CDCl3) δ: 7.84 (s, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.58-7.48 (m, 3H), 7.39-7.22 (m, 10H), 6.77 (s, 1H), 5.11 (s, 2H), 5.10 (s, 2H), 4.33 (t, J=7.6 Hz, 2H), 3.25 (t, J=6.0 Hz, 2H), 3.16 (s, 3H), 2.10-2.09 (m, 2H); LCMS: 575 [M+H].

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (15 ml×3)
  2. washthe combined organics were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-118ac4ff813f439988c863a7bfd10dea
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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