Dichloromethane → HCID 67262301, compound

HRID 410528Notes

Reaction equation

HRID 410528 reaction equation
[Si:1]([O:18][CH2:19][C:20]([C:23]1[S:24][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=2)=[CH:26][N:27]=1)([CH3:22])[CH3:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClCCl>C(OCC)(=O)C.[Pd]>[Si:1]([O:18][CH2:19][C:20]([C:23]1[S:24][C:25]([C:28]2[CH:29]=[C:30]([CH:31]=[CH:32][CH:33]=2)[NH2:34])=[CH:26][N:27]=1)([CH3:22])[CH3:21])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67432598HCID 67432598, compound

Product 1

HCID 67262301HCID 67262301, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Step 2 (461 mg, 0.892 mmol) in ethyl acetate (9 mL) was added Pd/C (10 wt %, 190 mg, 0.178 mmol), and the reaction vessel was charged with H2 (balloon) and stirred overnight, at which point LCMS analysis indicated complete conversion. Dichloromethane was added to deactivate the catalyst, and the mixture was filtered through a pad of Celite (ethyl acetate rinse) and concentrated in vacuo to provided 393 mg (0.807 mmol, 91%) of 3-[2-(1-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropan-2-yl)-1,3-thiazol-5-yl]aniline as a light yellow oil.

Workup

  1. additionthe reaction vessel was charged with H2 (balloon)
  2. filtrationthe mixture was filtered through a pad of Celite (ethyl acetate rinse)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69d36629a68e4533bbe1d2eff0a11b63
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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