4-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol ester → (2,5-Difluorophenyl)-{7-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl}-methanone

HRID 659367Notes

Reaction equation

HRID 659367 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13]2[N:17]=[CH:18][C:19](I)=[CH:20][C:12]1=2)=[O:10].[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]([C:31]2[CH:36]=[CH:35][C:34](B3OC(C)(C)C(C)(C)O3)=[CH:33][CH:32]=2)=[O:30])[CH2:25][CH2:24]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][NH:14][C:13]2[N:17]=[CH:18][C:19]([C:34]3[CH:33]=[CH:32][C:31]([C:29]([N:26]4[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]4)=[O:30])=[CH:36][CH:35]=3)=[CH:20][C:12]1=2)=[O:10]

Participants

3

Reactant 2

HCID 27600304-(4-Methylpiperazine-1-carbonyl)phenylboronic acid pinacol esterHCID 57885852(2,5-difluorophenyl)-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)methanone

Product 1

HCID 57885964(2,5-Difluorophenyl)-{7-[4-(4-methylpiperazine-1-carbonyl)phenyl]-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl}-methanoneYield 36%

Procedure

(2,5-Difluorophenyl)-(7-iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)methanone (35 mg) was reacted with (4-methylpiperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]methanone as in General Procedure 4A to give the title compound as a light yellow solid (36% yield). M.p. 201-203° C., LCMS: m/z=478.10 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.32 (s, 3H), 2.33-2.52 (m, 4H), 3.40-3.85 (m, 8H), 5.31 (s, 1H), 6.70-7.05 (m, 3H), 7.15 (s, 1H), 7.24-7.45 (m, 4H), 8.09 (s, 1H).

Sources & evidence

ORD record
ord-e485391b40a24ad98accb683b2a433f1
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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