1-Methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine → HCID 57886031, compound

HRID 659428Notes

Reaction equation

HRID 659428 reaction equation
[F:1][C:2]1[C:3]([C:20]([F:23])([F:22])[F:21])=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8]2[N:12]=[CH:13][C:14](I)=[CH:15][C:7]1=2.[CH3:24][N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][N:32]=2)[CH2:27][CH2:26]1>>[F:1][C:2]1[C:3]([C:20]([F:23])([F:22])[F:21])=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][C:8]2[N:12]=[CH:13][C:14]([C:34]3[CH:33]=[N:32][C:31]([N:28]4[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]4)=[CH:36][CH:35]=3)=[CH:15][C:7]1=2

Participants

3

Reactant 2

HCID 27696181-Methyl-4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazineHCID 57885822HCID 57885822, compound

Product 1

HCID 57886031HCID 57886031, compoundYield 31%

Procedure

1-[3-Fluoro-2-(trifluoromethyl)benzyl]-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (101 mg) was coupled to 1-methyl-4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl]piperazine as in General Procedure 4B to give the title compound as a yellow solid (31% yield). LCMS: m/z=487.09 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.33 (3H, s), 2.51 (4H, t, J=4.9 Hz), 3.49 (2H, m), 3.55 (4H, t, J=4.9 Hz), 3.63 (2H, m), 4.65 (2H, s), 5.08 (1H, bs), 6.48 (1H, d, J=1.8 Hz), 6.64 (1H, d, J=8.8 Hz), 7.09 (1H, m), 7.26 (1H, m), 7.45 (2H, m), 7.62 (1H, d, J=1.8 Hz), 8.18 (1H, d, J=2.5 Hz).

Sources & evidence

ORD record
ord-fa1ca1f9f0d546c99e11ddbb9cc1ecc9
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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