2-Cyanopyridine-5-boronic acid pinacol ester → 5-(8-Morpholino-2-(2-(quinolin-2-yl)ethynyl)imidazo[1,2-b]pyridazin-3-yl)picolinonitrile

HRID 718623Notes

Reaction equation

HRID 718623 reaction equation
Br[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[C:17]#[C:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[CH:39][C:40]([C:43]#[N:44])=[N:41][CH:42]=2)O1>>[O:14]1[CH2:15][CH2:16][N:11]([C:10]2[C:5]3[N:6]([C:2]([C:37]4[CH:38]=[CH:39][C:40]([C:43]#[N:44])=[N:41][CH:42]=4)=[C:3]([C:17]#[C:18][C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]=4)[N:4]=3)[N:7]=[CH:8][CH:9]=2)[CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 164141882-Cyanopyridine-5-boronic acid pinacol esterHCID 1177283744-(3-Bromo-2-(quinolin-2-ylethynyl)imidazo[1,2-b]pyridazin-8-yl)morpholine

Product 1

HCID 1177283575-(8-Morpholino-2-(2-(quinolin-2-yl)ethynyl)imidazo[1,2-b]pyridazin-3-yl)picolinonitrile

Procedure

Compound 18b (0.15 g, 0.35 mmol) was subjected to Suzuki coupling conditions with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile as described in Example 38, Step A to obtain compound 39a as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H19N2O: 458.2 (M+H). Found: 458.2.

Sources & evidence

ORD record
ord-298d9c22af7a4ae7922d0a4c80e9e41f
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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