Dimethyl Sulfide → HCID 136176942, compound

HRID 242211Notes

Reaction equation

HRID 242211 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=3)=[N:9][N:10]([CH3:14])[C:11]=2[CH:12]=[O:13])=[C:5]([CH3:23])[O:4][N:3]=1.[Li+].[BH4-].S(C)C>C(OCC)C>[CH3:1][C:2]1[C:6]([C:7]2[C:8]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[N:9][N:10]([CH3:14])[C:11]=2[CH2:12][OH:13])=[C:5]([CH3:23])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 4148881Lithium borohydrideHCID 86668982HCID 86668982, compound

Product 1

HCID 136176942HCID 136176942, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbaldehyde (4.1 mg, 0.013 mmol) in diethyl ether (3 mL) was added LiBH4 (12 mg, 0.55 mmol) and stirred at room temperature over night. The reaction was then quenched with water and extracted with EtOAc, filtered through a phase separator and concentrated. To the raw product in DCM (1 mL) was added BF3.Me2S (1 M solution in DCM, 0.2 mL, 0.2 mmol) and stirred over night at room temperature. The formed precipitate was twice washed with 0.5 mL DCM, dissolved in MeOH and purified on preparative HPLC to give E11 4-(4-(3,5-dimethylisoxazol-4-yl)-5-(hydroxymethyl)-1-methyl-1H-pyrazol-3-yl)phenol (2.8 mg, 0.009 mmol, 71%). ES/MS m/z: 299.6 (M+H), 297.7 (M−H); 1H NMR (MeOD, 500 MHz): 7.18 (m, 2H), 6.71 (m, 2H), 3.98 (s, 3H), 3.74 (s, 2H), 2.20 (s, 3H) and 1.87 (s, 3H).

Workup

  1. customThe reaction was then quenched with water
  2. extractionextracted with EtOAc
  3. filtrationfiltered through a phase separator
  4. concentrationconcentrated
  5. additionTo the raw product in DCM (1 mL) was added BF3
  6. washThe formed precipitate was twice washed with 0.5 mL DCM
  7. dissolutiondissolved in MeOH
  8. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-7e20da75da8748d0b22e48ea4d6e2b59
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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