Sodium Carbonate → HCID 57937830, compound

HRID 1435068Notes

Reaction equation

HRID 1435068 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[C:16]([F:21])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[C:29]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)#[N:30]>COCCOC>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([C:29]#[N:30])[CH:36]=2)=[C:16]([F:21])[CH:15]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 57937833HCID 57937833, compound

Product 1

HCID 57937830HCID 57937830, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(4-Bromo-3-fluoro-benzyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-5c: 1.5 g, 4.00 mmol) was dissolved in 1,2-dimethoxyethane (15 ml) under nitrogen. Palladium tetrakis(triphenylphospine) (5 mol %) was added followed by an aqueous 2 M sodium carbonate solution (7 ml) and 3-cyano-phenyl boronic acid (0.883 g, 6.01 mmol) was added. The reaction mixture was heated at reflux for 24 hours before being cooled to room temperature and filtered through Celite, rinsing with dimethoxyethane. The filtrate was concentrated under reduced pressure and the residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes to afford 1.25 g (78%) of title product (I-5d).

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 24 hours
  4. filtrationfiltered through Celite
  5. washrinsing with dimethoxyethane
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-c188104cf8754b33ae0295d28fc939be
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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