Sodium Bicarbonate → HCID 69561943, compound

HRID 1633866Notes

Reaction equation

HRID 1633866 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]=[C:23]3[CH:26]([CH3:28])[CH3:27])=[CH:18][CH:17]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]#[N:13])[CH:8]=[CH:7]2.[CH2:29]([OH:34])/[CH:30]=[CH:31]\[CH2:32][OH:33].C([O-])(O)=O.[Na+]>CN1CCCC1=O.Cl[Pd]Cl>[OH:33][CH2:32][CH2:31][CH:30]([C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][N:22]=[C:23]3[CH:26]([CH3:28])[CH3:27])=[CH:18][CH:17]=2)[CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([C:12]#[N:13])[CH:8]=[CH:7]2)[CH2:29][OH:34]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 6437902-Butene-1,4-diol, (2Z)-HCID 69561025HCID 69561025, compound

Product 1

HCID 69561943HCID 69561943, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A solution of Example 1K (3.09 g, 10 mmol) in N-methylpyrrolidinone (10 mL) was treated with PdCl2 (120 mg, 1 mmol), cis-2-butene-1,4-diol (1.23 mL, 15 mmol) and NaHCO3 (1.01 g, 12 mmol), heated to 130° C., stirred for 1 hour, cooled to room temperature, and purified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes to provide the desired product.

Workup

  1. temperaturecooled to room temperature
  2. custompurified by flash column chromatography on silica gel with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-12364d7ed47b48d8b1255b253e27755e
Source dataset
uspto-grants-2003_01
Patent number
US06504031B1

Reaction notes

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