Water → HCID 67135954, compound

HRID 1631037Notes

Reaction equation

HRID 1631037 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3C=CC(CO)=NC=3)[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]([F:30])([F:29])[F:28].CC[N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])C.CS([Cl:44])(=O)=O.O>C(Cl)Cl>[Cl:44][CH2:39][C:37]1[CH:38]=[C:13]([C:10]2[N:9]=[C:8]([C:6]3[CH:5]=[CH:4][C:3]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:30])([F:29])[F:28])=[C:2]([CH3:1])[CH:7]=3)[O:12][N:11]=2)[CH:36]=[CH:34][N:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67135200HCID 67135200, compound

Product 1

HCID 67135954HCID 67135954, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-(5-(2-methyl-2′-(trifluoromethyl)biphenyl-4-yl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methanol (0.103 g; 0.28 mmol) and DIEA (0.087 mL; 0.50 mmol) in DCM (2.5 mL) was added methanesulfonyl chloride (0.021 mL; 0.27 mmol). The mixture was stirred at ambient temperature for 1 hour and water added. The mixture was passed through a hydrophobic frit and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica, eluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc) to afford the title product (0.085 g, 79%). 1H NMR (CDCl3, 400 MHz) δ 8.78 (1 H, d, J=5.1 Hz), 8.25 (1 H, s), 8.15 (1 H, s), 8.08 (1 H, dd, J=8.0, 1.7 Hz), 8.01 (1 H, dd, J=5.0, 1.5 Hz), 7.81 (1 H, d, J=8.0 Hz), 7.63 (1 H, t, J=7.6 Hz), 7.54 (1 H, t, J=7.8 Hz), 7.36 (1 H, d, J=7.9 Hz), 7.29-7.23 (1 H, m), 4.79 (2 H, s), 2.16 (3 H, s).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe residue was purified by flash chromatography on silica
  3. washeluting with iso-hexane/EtOAc (100% iso-hexane to 100% EtOAc)

Sources & evidence

ORD record
ord-6182d5e5949546b8a9f7db82d19c340d
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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