Ethyl 3-amino-6-bromopicolinate → ethyl 3-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]pyridine-2-carboxylate

HRID 2279750Notes

Reaction equation

HRID 2279750 reaction equation
NC1C=CC(C2C=NN(CCCO)C=2)=CC=1C(N(CC)CC)=O.[CH2:24]([O:26][C:27]([C:29]1[C:34]([NH2:35])=[CH:33][CH:32]=[C:31](Br)[N:30]=1)=[O:28])[CH3:25].CC1(C)C(C)(C)OB([C:45]2[CH:46]=[N:47][N:48]([CH2:50][CH2:51][CH2:52][CH2:53][OH:54])[CH:49]=2)O1>>[NH2:35][C:34]1[C:29]([C:27]([O:26][CH2:24][CH3:25])=[O:28])=[N:30][C:31]([C:45]2[CH:46]=[N:47][N:48]([CH2:50][CH2:51][CH2:52][CH2:53][OH:54])[CH:49]=2)=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 25137688Ethyl 3-amino-6-bromopicolinate2×HCID 678147924-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-olHCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 86697704ethyl 3-amino-6-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]pyridine-2-carboxylateYield 55%

Procedure

Prepared analogously to Compound 3C using 3-amino-6-bromopyridine-2-carboxylic acid ethyl ester (Compound 6E, 300 mg, 1.22 mmol) and 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-ol (Compound 14C, 358 mg, 1.35 mmol) to afford 196 mg of the title compound (55%). 1H NMR (400 MHz, CDCl3) δ 8.12 (br. s., 1H), 7.87 (s, 1H), 7.81 (s, 1H), 7.36 (d, J=8.6 Hz, 1H), 7.03 (d, J=8.6 Hz, 1H), 5.94 (br. s., 2H), 4.23 (t, J=6.9 Hz, 2H), 3.70 (q, J=5.9 Hz, 2H), 3.03 (d, J=5.1 Hz, 3H), 2.03 (quin, J=7.3 Hz, 2H), 1.60-1.67 (m, 3H) [OH proton obscured].

Sources & evidence

ORD record
ord-d00d8c90525740ae90f0366ea1e776f9
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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