Imidazole → HCID 67390409, compound

HRID 905532Notes

Reaction equation

HRID 905532 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1.[CH3:20][CH:21]([Si:23](Cl)([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH3:22].N1C=CN=C1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[CH2:10][S:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si:23]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:22])[CH3:20])[CH:13]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 67391415HCID 67391415, compound

Product 1

HCID 67390409HCID 67390409, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 100 mL three-neck round bottom flask was added 9n (1.4 g, 5 mmol) and TIPSCl (1.15 g, 6 mmol) in CH2Cl2 (40 mL) under nitrogen at room temperature. Then a solution of imidazole (816 mg, 12 mmol) in CH2Cl2 (20 mL) was added dropwise. The resulting mixture was stirred for 24 h. The mixture was filtered and the solvents were removed under reduced pressure. The residue was purified by flash column chromatography eluted by hexane:ethyl acetate (6:1) and the correct product was obtained as a slightly yellow oil; yield 96% (2.1 g); H NMR (400 MHz, CDCl3): d 1.13 (m, 18H, 6×CH3), 1.29 (m, 3H, CH), 4.26 (s, 2H, SCH2), 6.75 (m, 1H, Ar), 6.89-6.97 (m, 4H, Ar), 7.15 (m, 1H, Ar), 7.95 (m, 1H, Ar); CNMR (100 MHz, CDCl3): δ 21.6, 17.7, 29.3, 104.3, 111.5, 118.5, 119.2, 121.5, 122.7, 129.5, 131.4, 135.9, 153.6, 156.3, 159.5, 162.3, 164.9; IR ν (cm−1) 2944, 2983, 2866, 1682, 1610, 1584, 1475, 1423, 1266, 1245, 1186, 1145, 1095, 997, 970, 943, 881, 852, 776, 683; ESI HRMS m/z calcd for C23H31F2O3SSi (M+OH)+ 453.17258, found 453.17226.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvents were removed under reduced pressure
  3. customThe residue was purified by flash column chromatography
  4. washeluted by hexane:ethyl acetate (6:1)
  5. customthe correct product was obtained as a slightly yellow oil

Sources & evidence

ORD record
ord-72056b8dc21f40cba77a26043d527fb4
Source dataset
uspto-grants-2011_09
Patent number
US08012901B1

Reaction notes

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