Sodium Bicarbonate → Tert-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)-1,4-diazepane-1-carboxylate

HRID 2206333Notes

Reaction equation

HRID 2206333 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[N:3]=1.[N:11]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C([O-])(O)=O.[Na+]>CS(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([N:14]2[CH2:15][CH2:16][CH2:17][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12][CH2:13]2)=[N:3][C:4]=1[OH:10])=[O:7]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 178519593HCID 178519593, compound

Product 1

HCID 178452079Tert-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)-1,4-diazepane-1-carboxylateYield 102.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-2-hydroxynicotinaldehyde (1 g, 6.37 mmol) was dissolved in DMSO (12 mL) at room temperature. The solution was treated with tert-butyl 1,4-diazepane-1-carboxylate (2.55 g, 12.74 mmol) at room temperature. The reaction mixture was stirred at 100° C. for 2 hours and cooled to room temperature. An aqueous saturated NaHCO3 solution (50 mL) was added. The aqueous layer was extracted with CH2Cl2 three times. The combined organic layers were dried over K2CO3, filtered and concentrated under vacuum to give 2.1 g of tert-butyl 4-(5-formyl-6-hydroxypyridin-2-yl)-1,4-diazepane-1-carboxylate. The concentrated residue was used in next step without further purification. MS m/z 322 [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous layer was extracted with CH2Cl2 three times
  3. dry with materialThe combined organic layers were dried over K2CO3
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-75cca1fd025e4c12bdfd3259d1840e85
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

Loading…