Cesium carbonate → HCID 131735973, compound

HRID 2209032Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][C@@H:9]([C@H:11]2[CH2:15][N:14]([C@@H:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH3:17])[C:13](=[O:26])[CH2:12]2)[CH3:10])[C:5]2[N:27]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:28]([CH3:30])=[N:29][C:4]=2[CH:3]=1.[CH3:39][O:40][C:41]1[CH:42]=[C:43](B(O)O)[CH:44]=[CH:45][C:46]=1[O:47][CH3:48].C([O-])([O-])=O.[Cs+].[Cs+].C1OCCOC1>O>[CH3:39][O:40][C:41]1[CH:42]=[C:43]([C:2]2[N:7]=[C:6]([O:8][C@@H:9]([C@H:11]3[CH2:15][N:14]([C@@H:16]([C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)[CH3:17])[C:13](=[O:26])[CH2:12]3)[CH3:10])[C:5]3[N:27]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:28]([CH3:30])=[N:29][C:4]=3[CH:3]=2)[CH:44]=[CH:45][C:46]=1[O:47][CH3:48]

Participants

Conditions

Temperature: 100 °C

Procedure

To a (R)-4-((R)-1-(6-chloro-2-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one 2.65B (1 eq), 3,4-dimethoxy phenyl boronic acid (1.3 eq), Cs2CO3 (3.0 eq) and PEPPSI″-IPr catalyst (0.1 eq) was added 1-4 Dioxane and water (2:1) and the reaction was heated to 100° C. for 1 hr. The reaction mixture was concentrated and purified by normal phase chromatography (Hexanes:Acetone 1:1) to afford (R)-4-((R)-1-(6-(3,4-dimethoxyphenyl)-2-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridin-4-yloxy)ethyl)-1-((R)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one.[M+H]+ calcd C36H48N4O6Si: 661.33; found 661.3

Workup

concentrationThe reaction mixture was concentrated
custompurified by normal phase chromatography (Hexanes:Acetone 1:1)

Sources & evidence

ORD record: ord-c4a7deecd14743268037863eacc15b38
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376441B2

Reaction notes

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