2-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol ester → 7-[2-(4-Methylpiperazin-1-yl)pyridin-4-yl]-1-[5-(trifluoromethyl)furan-2-ylmethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 659475Notes

Reaction equation

HRID 659475 reaction equation
I[C:2]1[CH:21]=[N:20][C:5]2[NH:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]3[O:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=3)[C:4]=2[CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:32]=[CH:31][N:30]=2)[CH2:25][CH2:24]1>>[CH3:22][N:23]1[CH2:24][CH2:25][N:26]([C:29]2[CH:34]=[C:33]([C:2]3[CH:21]=[N:20][C:5]4[NH:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]5[O:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=5)[C:4]=4[CH:3]=3)[CH:32]=[CH:31][N:30]=2)[CH2:27][CH2:28]1

Participants

3

Reactant 2

HCID 27695372-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol esterHCID 578858467-Iodo-1-[5-(trifluoromethyl)furan-2-ylmethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 578861027-[2-(4-Methylpiperazin-1-yl)pyridin-4-yl]-1-[5-(trifluoromethyl)furan-2-ylmethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazineYield 30%

Procedure

7-Iodo-1-[5-(trifluoromethyl)furan-2-ylmethyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (60 mg) was reacted with 1-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl]piperazine as in General Procedure 4A to give the title compound as a beige foam (30% yield). M.p. (foam), 1H-NMR (CDCl3, 400 MHz) δ 2.31-3.36 (m, 4H), 2.38-2.53 (m, 4H), 3.42-3.48 (m, 2H), 3.48-3.58 (m, 1H), 3.61-3.66 (m, 2H), 3.74-3.84 (m, 2H), 5.02 (bs, 1H), 6.31 (s, 1H), 6.74 (s, 1H), 6.93 (s, 1H), 7.41-7.50 (m, 3H), 7.73 (s, 1H).

Sources & evidence

ORD record
ord-b31b37134b664332939456f3e4bf2ad7
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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