Cesium fluoride → HCID 57835769, compound

HRID 731187Notes

Reaction equation

HRID 731187 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([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)[CH2:6][CH2:5]2.[CH2:27]([O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)[CH3:28].[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>[CH2:27]([O:29][C:30]1[CH:35]=[C:34]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH:7]([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)[CH2:6][CH2:5]3)[CH:33]=[CH:32][CH:31]=1)[CH3:28]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27739203-Ethoxybenzeneboronic acidHCID 57835766HCID 57835766, compound

Product 1

HCID 57835769HCID 57835769, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 59.2 (30 mg, 0.073 mmol), 3-ethoxyphenylboronic acid (14.5 mg, 0.087 mmol) and CsF (55 mg, 0.36 mmol) in 1,2-dimethoxyethane (2 mL) was degassed with N2 for 3 minutes. Pd(PPh3)4 (20 mg, 0.017 mmol) was added, and the resulting mixture was heated to 95° C. for 8 hours. After cooling, the reaction mixture was quenched with water and extracted with EtOAc to obtain the ester 59.3, which was directly hydrolyzed in 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

Sources & evidence

ORD record
ord-e92d65de3bef419da989b44fb9297ef4
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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