3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → 2-[[8-(4-Morpholinyl)-5-(3-pyridinyl)imidazo[1,2-a]pyrazin-2-yl]methoxy]quinoline

HRID 1772685Notes

Reaction equation

HRID 1772685 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O: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.[N:29]1[CH:34]=[CH:33][CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=1>>[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([C:2]2[N:7]3[CH:8]=[C:9]([CH2:11][O: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]=[C:6]3[C:5]([N:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[N:4][CH:3]=2)[CH:30]=1

Participants

3

Reactant 2

HCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 117728336HCID 117728336, compound

Product 1

HCID 863457682-[[8-(4-Morpholinyl)-5-(3-pyridinyl)imidazo[1,2-a]pyrazin-2-yl]methoxy]quinoline

Procedure

Compound 15a (150.0 mg, 0.34 mmol) was subjected to Suzuki coupling conditions with 3-pyridineboronic acid pinacol ester using the methods described in Example 1, Step G to obtain compound 46a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C25H22N6O2: 439.1 (M+H). Found 439.1.

Sources & evidence

ORD record
ord-afbf589ab45c4743afb3aac3230cb4bb
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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