Dimethyl Sulfide → HCID 136176946, compound

HRID 242217Notes

Reaction equation

HRID 242217 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)[C:12]=1[C:25]1[C:26]([CH3:31])=[N:27][O:28][C:29]=1[CH3:30])(C(C)(C)C)(C)C.B(F)(F)F.S(C)C>C(Cl)Cl>[CH3:31][C:26]1[C:25]([C:12]2[C:13]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)=[N:14][N:15]([CH3:16])[C:11]=2[CH2:10][CH2:9][OH:8])=[C:29]([CH3:30])[O:28][N:27]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 6356Boron trifluorideHCID 67120058HCID 67120058, compound

Product 1

HCID 136176946HCID 136176946, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(5-(2-(tert-butyldimethylsilyloxy)ethyl)-3-(4-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl)-3,5-dimethylisoxazole (41.5 mg, 0.094 mmol) in DCM (3 ml) was added BF3.Me2S (1 M solution in DCM, 0.5 mL, 0.5 mmol) and the mixture was stirred at room temperature over night. The DCM layer was discarded and the precipitate was washed with another 0.2 ml DCM. The raw product was purified on silica gel to give 4-(4-(3,5-dimethylisoxazol-4-yl)-5-(2-hydroxyethyl)-1-methyl-1H-pyrazol-3-yl)phenol (28.6 mg, 0.091 mmol, 97%) ES/MS m/z: 314.22 (M+H), 312.31 (M−H); 1H NMR (MeOD, 500 MHz): 7.15 (m, 2H), 6.70 (m, 2H), 3.88 (s, 3H), 3.54 (t, 2H, J=6.8 Hz), 2.70 (t, 2H, J=6.8 Hz), 2.16 (s, 3H) and 1.87 (s, 3H).

Workup

  1. washthe precipitate was washed with another 0.2 ml DCM
  2. customThe raw product was purified on silica gel

Sources & evidence

ORD record
ord-179a5c20405049c787ba63433fbd65d7
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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