1,1-Dichloroethane → HCID 59525703, compound

HRID 385819Notes

Reaction equation

HRID 385819 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.Cl.[CH2:11]([O:13][C:14](=[O:17])[CH2:15][NH2:16])[CH3:12].ClC(Cl)C.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:16][CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:17])[CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 63651,1-DichloroethaneHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59525703HCID 59525703, compound

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

6-Bromopyridine-2-carbaldehyde (10 g, 53.8 mmol) and glycine ethyl ester hydrochloride (7.50 g, 53.8 mmol) were placed in a flask. Dichloroethane (220 mL) and triethylamine (7.49 mL, 53.8 mmol) were added and the reaction was stirred for 45 minutes. Sodium triacetoxyborohydride (15.95 g, 75 mmol) was added and the reaction was stirred at ambient temperature overnight. The reaction was diluted with ethyl acetate, saturated sodium bicarbonate, and saturated sodium carbonate to make the pH basic. The organic layer was separated and washed with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Workup

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-701f12d4aade4e40aa66ec8deccea836
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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