Cesium fluoride → HCID 69291901, compound

HRID 1247434Notes

Reaction equation

HRID 1247434 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([C:9]1[C:14]([F:15])=[CH:13][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][C:10]=1[F:25])[O:6][CH2:7][CH3:8])[CH3:2].[NH2:27][C:28]1[CH:33]=[CH:32][C:31](Br)=[CH:30][N:29]=1.[F-].[Cs+]>COCCOC>[CH2:1]([O:3][C:4](=[O:26])[CH:5]([C:9]1[C:10]([F:25])=[CH:11][C:12]([C:31]2[CH:30]=[N:29][C:28]([NH2:27])=[CH:33][CH:32]=2)=[CH:13][C:14]=1[F:15])[O:6][CH2:7][CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 706222-Amino-5-bromopyridineHCID 69290159Ethyl α-ethoxy-2,6-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzeneacetate

Product 1

HCID 69291901HCID 69291901, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (RS)-[2,6-difluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethoxy-acetic acid ethyl ester in 1,2-dimethoxyethane was treated with 2-amino-5-bromopyridine and CsF. The reaction mixture was deoxygenated by passing a stream of argon through it. Tetrakis(triphenylphosphine)palladium(0) was added. The reaction mixture was heated to 80° for 2 days, then cooled to rt and concentrated. The crude product was isolated by flash chromatography (cyclohexane/EtOAc 2:1=>EtOAc) to give (RS)-[4-(6-amino-pyridin-3-yl)-2,6-difluoro-phenyl]-ethoxy-acetic acid ethyl ester as amorphous brown solid.

Workup

  1. customThe reaction mixture was deoxygenated
  2. additionTetrakis(triphenylphosphine)palladium(0) was added
  3. temperatureThe reaction mixture was heated to 80° for 2 days
  4. concentrationconcentrated
  5. customThe crude product was isolated by flash chromatography (cyclohexane/EtOAc 2:1=>EtOAc)

Sources & evidence

ORD record
ord-6e93b809c45b47bcbeeab50ac6a5353a
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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