5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,3-diamine → (E)-5-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridine-2,3-diamine

HRID 1772600Notes

Reaction equation

HRID 1772600 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[C:39]([NH2:44])[C:40]([NH2:43])=[N:41][CH:42]=2)O1>>[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9](/[CH:11]=[CH:12]/[C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:37]3[CH:38]=[C:39]([NH2:44])[C:40]([NH2:43])=[N:41][CH:42]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 467380085-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,3-diamineHCID 117728505(E)-4-(5-Bromo-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 117728025(E)-5-(8-Morpholino-2-(2-(quinolin-2-yl)vinyl)imidazo[1,2-a]pyrazin-5-yl)pyridine-2,3-diamineYield 54.3%

Procedure

Compound 2b (1.00 g, 2.30 mmol, as prepared in Example 2, Step B) was subjected to Suzuki coupling conditions with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2,3-diamine (1.62 g, 6.91 mmol) using the reaction conditions described in Example 1, Step G to obtain compound 6b (580 mg, 51% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C26H24N8O: 465.2 (M+H). Found 465.3.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-95ca4c9214c748e59d14bd78a1f6f9d1
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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