3,3-Diethoxy-1-propene → HCID 22118874, compound

HRID 1275053Notes

Reaction equation

HRID 1275053 reaction equation
B1C2CCCC1CCC2.[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH:14]=[CH2:15])[CH3:11].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:28]1[CH:37]=[N:36][C:31]2=[N:32][CH:33]=[CH:34][N:35]=[C:30]2[CH:29]=1>O1CCCC1.C1C=CC=CC=1>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][CH2:15][C:28]1[CH:37]=[N:36][C:31]2=[N:32][CH:33]=[CH:34][N:35]=[C:30]2[CH:29]=1)[CH3:11]

Participants

7

Reactant 4

HCID 624773,3-Diethoxy-1-propeneHCID 62657Potassium Phosphate, TribasicHCID 789669-Borabicyclo(3.3.1)nonaneHCID 42469437-bromopyrido[2,3-b]pyrazine

Product 1

HCID 22118874HCID 22118874, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9-BBN (10.2 mL of a 0.5M solution in tetrahydrofuran) at 0° C. was added dropwise 0.77 mL of acrolein diethyl acetal and the mixture allowed to warm slowly to room temperature. After 15 hours, the mixture was diluted with 12 mL dry tetrahydrofuran followed by the sequential addition of potassium phosphate (1.6 g), palladium(1,1'-bis(diphenylphosphino)ferrocenyl) dichloride (160 mg) and 7-bromo-pyrido[2,3-b]pyrazine (924 mg) and then heated to reflux on an oil bath. After 5 hours, the mixture was cooled to 0° C., diluted with 15 mL benzene and the excess reagents quenched by the addition of 2N sodium hydroxide (3.5 mL) and 30% hydrogen peroxide (2.5 mL). The mixture then extracted with ethyl acetate, washed with brine and the concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:4; then 1:1; then 4:1) to give the title compound (1.2 g).

Workup

  1. temperatureheated
  2. temperatureto reflux on an oil bath
  3. waitAfter 5 hours
  4. temperaturethe mixture was cooled to 0° C.
  5. customthe excess reagents quenched by the addition of 2N sodium hydroxide (3.5 mL) and 30% hydrogen peroxide (2.5 mL)
  6. extractionThe mixture then extracted with ethyl acetate
  7. washwashed with brine
  8. customthe concentrate purified by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-e7f9829c32e74a57b198afc45ced2a01
Source dataset
uspto-grants-2000_12
Patent number
US06159975

Reaction notes

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