4-(3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2-YL)morpholine → 1-(2-Chloro-3,6-difluorobenzyl)-7-(3-fluoro-2-morpholin-4-yl-pyridin-4-yl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

HRID 659375Notes

Reaction equation

HRID 659375 reaction equation
[Cl:1][C:2]1[C:19]([F:20])=[CH:18][CH:17]=[C:16]([F:21])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13](I)=[CH:14][C:6]1=2.[F:22][C:23]1[C:24]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[N:25][CH:26]=[CH:27][C:28]=1B1OC(C)(C)C(C)(C)O1>>[Cl:1][C:2]1[C:19]([F:20])=[CH:18][CH:17]=[C:16]([F:21])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C:7]2[N:11]=[CH:12][C:13]([C:28]3[CH:27]=[CH:26][N:25]=[C:24]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)[C:23]=3[F:22])=[CH:14][C:6]1=2

Participants

3

Reactant 2

HCID 164142374-(3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridin-2-YL)morpholineHCID 578858681-(2-Chloro-3,6-difluorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine

Product 1

HCID 578858161-(2-Chloro-3,6-difluorobenzyl)-7-(3-fluoro-2-morpholin-4-yl-pyridin-4-yl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazineYield 35%

Procedure

1-(2-Chloro-3,6-difluorobenzyl)-7-iodo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (100 mg) was reacted with 4-[3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridin-2-yl]morpholine as in General Procedure 4A to give the title compound as a tan foam (35% yield). M.p. (foam), LCMS: m/z=476.02 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.28 (t, J=4.8 Hz, 2H), 3.48 (t, J=4.8 Hz, 4H), 3.52-3.65 (m, 2H), 3.87 (t, J=4.6 Hz, 4H), 4.50 (s, 2H), 5.38 (bs, 1H), 6.82-6.86 (m, 1H), 6.97-7.04 (m, 1H), 7.08 (s, 1H), 7.04-7.15 (m, 1H), 7.70 (s, 1H), 8.00 (d, J=5.0 Hz, 1H).

Sources & evidence

ORD record
ord-9255f26d278a46e28000bb3c8b1b494e
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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