1,4-Benzenedimethanol → HCID 67159328, compound

HRID 1255170Notes

Reaction equation

HRID 1255170 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1.[C:28]1([CH2:36]O)[CH:33]=[CH:32][C:31]([CH2:34][OH:35])=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[OH:35][CH2:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:36][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[N:13]=[C:12]([N:14]3[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]3)[CH:11]=[CH:10][CH:9]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 115061,4-BenzenedimethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136298134Ethyl 1-[6-(2-hydroxylphenyl)pyridine-2-yl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate

Product 1

HCID 67159328HCID 67159328, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the title compound of Example 1 Step B (150 mg, 0.40 mmol) and 1,4-benzenedimethanol (165 mg, 1.19 mmol) in THF (2 mL) were added triphenylphosphine (313 mg, 1.19 mmol), followed by diisopropyl azodicarboxylate (0.232 mL, 1.19 mmol). The reaction vial was capped and stirred at 60° C. After 1.5 h, the reaction mixture was allowed to cool to ambient temperature, then was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 40% EtOAc in hexanes, then 40 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 498.1 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.13 (d, J=8.0 Hz, 1H), 8.12 (s, 1H), 7.95 (dd, J=8.0, 1.5 Hz, 1H), 7.85 (t, J=7.5 Hz, 1H), 7.51 (d, J=8.5 Hz, 1H), 7.39-7.28 (m, 5H), 7.11 (t, J=7.5 Hz, 1H), 7.06 (d, J=7.5 Hz, 1H), 5.15 (s, 2H), 4.98-4.94 (m, 2H), 4.38 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.0 Hz, 3H).

Workup

  1. customThe reaction vial was capped
  2. temperatureto cool to ambient temperature
  3. concentrationwas concentrated in vacuo
  4. customPurification by flash chromatography on silica gel (0 to 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-bde6ea007a0642378137282fc8ee9ee9
Source dataset
uspto-grants-2013_06
Patent number
US08455638B2

Reaction notes

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