Cesium fluoride → HCID 86717532, compound

HRID 712074Notes

Reaction equation

HRID 712074 reaction equation
Br[C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:3]=1.C[Sn](C)(C)[C:18]1[S:19][CH:20]=[CH:21][C:22]=1[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].[F-].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:7][C:5]1[N:4]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:3]=[C:2]([C:18]2[S:19][CH:20]=[CH:21][C:22]=2[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH:6]=1

Participants

7

Reactant 4

HCID 25953Cesium fluorideHCID 103612511,1-Dimethylethyl N-[2-(trimethylstannyl)-3-thienyl]carbamateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86717531HCID 86717531, compound

Product 1

HCID 86717532HCID 86717532, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A microwave vial charge with 3-bromo-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazole (2.99 g, 10.3 mmol), tert-butyl [2-(trimethylstannyl)-3-thienyl]carbamate (4.40 g, 11.3 mmol), cesium fluoride (3.4 g, 23 mmol) and pre-milled palladium acetate and dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (190 mg, 0.20 mmol) was purged with nitrogen three times. 1,2-Dimethoxyethane (10 mL) was added and resulting suspension was heated at 80° C. overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate and filtered through a pad of silica gel. The silica gel pad was washed with ethyl acetate. The solvent was removed in vacuo and the residue was purified with flash chromatography (eluting with a gradient of 0-20% ethyl acetate in hexanes) to give the desired product. LCMS calculated for C19H32N3O3SSi (M+H)+: m/z=410.2. Found: 410.2.

Workup

  1. customwas purged with nitrogen three times
  2. addition1,2-Dimethoxyethane (10 mL) was added
  3. customresulting suspension
  4. temperatureAfter cooling to room temperature
  5. filtrationfiltered through a pad of silica gel
  6. washThe silica gel pad was washed with ethyl acetate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified with flash chromatography (
  9. washeluting with a gradient of 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c11bc92c21a5429ebae24561a2154ac5
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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