Cesium fluoride → HCID 86611518, compound

HRID 731177Notes

Reaction equation

HRID 731177 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[O:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18]([C:24]#[C:25][CH3:26])[CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.[F-].[Cs+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:27][C:28]([F:39])([F:38])[C:29]1[CH:30]=[C:31]([C:10]2[CH:2]=[C:3]3[C:7](=[CH:8][CH:9]=2)[CH:6]([O:11][C:12]2[CH:13]=[CH:14][C:15]([C@@H:18]([C:24]#[C:25][CH3:26])[CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:17]=2)[CH2:5][CH2:4]3)[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57835840HCID 57835840, compound

Product 1

HCID 86611518HCID 86611518, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1.3 (74 mg, 0.18 mmol), 4-(trifluoromethyl)phenylboronic acid (45.8 mg, 0.22 mmol) and CsF (56 mg, 0.37 mmol) in 1,2-dimethoxyethane (2 mL), was degassed with N2 for 3 minutes. Pd(PPh3)4 (21 mg, 0.018 mmol) was added, and the resulting mixture was heated at 95° C. for 8 hours. After cooling, the reaction mixture was quenched with water and extracted with EtOAc providing 1.4 (20 mg), which was directly hydrolyzed in the next step.

Workup

  1. customwas degassed with N2 for 3 minutes
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched with water
  4. extractionextracted with EtOAc providing 1.4 (20 mg), which

Sources & evidence

ORD record
ord-c9eb5407d07e415d980682c50656191f
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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