Triethylamine → HCID 86682736, compound

HRID 1755385Notes

Reaction equation

HRID 1755385 reaction equation
F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[C:9]([CH:13]1[CH2:17][CH2:16][NH:15][CH2:14]1)([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>O>[C:9]([CH:13]1[CH2:17][CH2:16][N:15]([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=2)[CH2:14]1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27613996-Fluoropyridin-2-amineHCID 235608703-tert-Butylpyrrolidine

Product 1

HCID 86682736HCID 86682736, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 6-fluoropyridin-2-amine (500 mg, 4.46 mmol), 3-tert-butylpyrrolidine (730 mg, 4.46 mmol) in water (0.5 mL) and triethylamine (0.9 g, 8.92 mmol) was heated to 150° C. in a microwave oven for 30 minutes. The reaction mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=20:1) to give 6-(3-tert-butylpyrrolidin-1-yl)pyridin-2-amine (540 mg, 55%) as a brown oil. LC-MS: [M+H]+, 220, tR=1.228 min.

Workup

  1. customThe reaction mixture was purified by chromatography (silica gel, 200-300 mesh, dichloromethane:MeOH=20:1)

Sources & evidence

ORD record
ord-a1c9c9fc83624637b71b11f63516e281
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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