4-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholine → 3,3-Difluoro-5-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)indolin-2-one
Reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][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.[F:29][C:30]1([F:57])[C:38]2[C:33](=[CH:34][CH:35]=[C:36](B3OC(C)(C)C(C)(C)O3)[CH:37]=2)[N:32]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[C:31]1=[O:56]>>[F:29][C:30]1([F:57])[C:38]2[C:33](=[CH:34][CH:35]=[C:36]([C:2]3[N:7]4[CH:8]=[C:9]([CH2:11][CH2:12][C:13]5[CH:22]=[CH:21][C:20]6[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=6)[N:14]=5)[N:10]=[C:6]4[C:5]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[N:4][CH:3]=3)[CH:37]=2)[N:32]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:53])[CH3:54])[C:31]1=[O:56]Participants
3
Reactant 2
Product 1
Procedure
Compound 3a was subjected to Suzuki coupling conditions with 3,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2(trimethylsilyl)ethoxy)methyl)indolin-2-one to obtain compound 37b using the method described in the Example 21, Step D. Mass Spectrum (LCMS, ESI pos.) Calcd. For C35H38F2N6O3Si: 657.2 (M+H). Found 657.5.
Sources & evidence
- ORD record
- ord-68bae188b37e481f9de5ebedfc7a96ff
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249163B2
Reaction notes
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