4-Fluorobenzylamine → 5-(Aminomethyl)-pyridine-2-carboxylic acid 4-fluoro-benzylamide

HRID 911298Notes

Reaction equation

HRID 911298 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C(OC([NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]([O-])=[O:26])=[N:23][CH:24]=1)=O)(C)(C)C.[Li+].CCN(C(C)C)C(C)C>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:25]([C:22]2[CH:21]=[CH:20][C:19]([CH2:18][NH2:17])=[CH:24][N:23]=2)=[O:26])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 673264-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 57656023Lithium 5-(tert-butoxycarbonylamino-methyl)-pyridine-2-carboxylate

Product 1

HCID 576560665-(Aminomethyl)-pyridine-2-carboxylic acid 4-fluoro-benzylamideYield 26.3%

Procedure

Use the General Procedure 6-2, using 4-fluoro-benzylamine (551 mg, 4.4 mmol), lithium 5-(tert-butoxycarbonylamino-methyl)-pyridine-2-carboxylate (740 mg, 2.93 mmol) and DIEA (2.6 mL) as cosolvent, to give the title compound as a white solid (200 mg, 26%). MS (ES+) m/z: 260 (M+H)+.

Sources & evidence

ORD record
ord-4238abacbaa5438099cf3a23e75d3598
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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