Water → tert-Butyl 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 1475353Notes

Reaction equation

HRID 1475353 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([CH3:12])([CH3:11])[CH2:9][NH:10][C:4]=2[CH:3]=1.[C:13](OC([O-])=O)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].O>C1COCC1.CN(C)C1C=CN=CC=1>[C:16]([O:15][C:13]([N:10]1[C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[CH:6][C:5]=2[C:8]([CH3:12])([CH3:11])[CH2:9]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 22064466Tert-butyldicarbonateHCID 86723967HCID 86723967, compound

Product 1

HCID 86723969tert-Butyl 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylateYield 49.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine (1.3 g, 7.4 mmol) in THF (20 mL) were added tert-butyl dicarbonate (4.1 g, 18.6 mmol) and dimethyl-pyridin-4-yl-amine (2.22 g, 18.6 mmol) and the solution was stirred for 2 h. Water (60 mL) was added and the product was extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and evaporated. Chromatography (SiO2, eluted with petrol-EtOAc 0-40%) gave the title compound (1.04 g). 1H NMR (Me-d3-OD): 8.04 (1H, s), 7.60 (1H, s), 3.81 (2H, s), 1.59 (9H, s), 1.40 (6H, s). MS: [M+H]+=283.

Workup

  1. extractionthe product was extracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. washChromatography (SiO2, eluted with petrol-EtOAc 0-40%)

Sources & evidence

ORD record
ord-818e8119702a48148756e1e4d4c74282
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…