Diisopropylethylamine → HCID 90456915, compound

HRID 1770794Notes

Reaction equation

HRID 1770794 reaction equation
F[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7]C)=[O:5].C(N(C(C)C)CC)(C)C.[CH:22]12[O:29][CH:26]([CH2:27][CH2:28]1)[CH2:25][NH:24][CH2:23]2>CN1C(=O)CCC1>[CH:26]12[O:29][CH:22]([CH2:28][CH2:27]1)[CH2:23][N:24]([C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH2:25]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 120692318-Oxa-3-azabicyclo[3.2.1]octaneHCID 14296371Ethyl 2-fluoropyridine-3-carboxylate

Product 1

HCID 90456915HCID 90456915, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of ethyl 2-fluoronicotinate (0.15 g, 0.97 mmol) in NMP (0.5 mL) was added diisopropylethyl amine (0.50 mL, 2.9 mmol), and 8-oxa-3-azabicyclo[3.2.1]octane (0.17 g, 0.72 mmol). The resulting mixture was irradiated with microwaves (100° C.) for 1 h and loaded directly onto a silica column. Eluting the column with EtOAc/hexanes (0-100%) provided methyl 2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)nicotinate as a clear oil (0.100 g, 42% yield). MS (ES) for C13H16N2O3: 249 (MH+).

Workup

  1. customThe resulting mixture was irradiated with microwaves (100° C.) for 1 h
  2. washEluting the column with EtOAc/hexanes (0-100%)

Sources & evidence

ORD record
ord-f901caf0b8eb424ea0dfcce94bcf1dfc
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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