5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one → 5-(3-Tert-butyl-5-(2,4-di-tert-butoxypyrimidin-5-yl)-2-methoxy phenyl)-2,3-dihydro-1h-inden-1-one
Reaction equation
Br[C:2]1[CH:3]=[C:4]([C:14]2[C:15]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:16][C:17]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:18][CH:19]=2)[CH:5]=[C:6]([C:10]([CH3:13])([CH3:12])[CH3:11])[C:7]=1[O:8][CH3:9].CC1(C)C(C)(C)OB([C:38]2[CH:39]=[C:40]3[C:44](=[CH:45][CH:46]=2)[C:43](=[O:47])[CH2:42][CH2:41]3)O1>>[C:10]([C:6]1[C:7]([O:8][CH3:9])=[C:2]([C:38]2[CH:39]=[C:40]3[C:44](=[CH:45][CH:46]=2)[C:43](=[O:47])[CH2:42][CH2:41]3)[CH:3]=[C:4]([C:14]2[C:15]([O:25][C:26]([CH3:29])([CH3:27])[CH3:28])=[N:16][C:17]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[N:18][CH:19]=2)[CH:5]=1)([CH3:12])([CH3:13])[CH3:11]Participants
3
Procedure
A solution of Example 2 Part A (0.150 g, 0.32 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one (0.092 g, 0.36 mmol) were reacted in the same manner as Example 50 Part A using 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex as catalyst at 100° C. for 1.5 hours in the microwave and for 4 hours at 100° C. in an oil bath to give crude product which was purified by silica gel flash chromatography eluting with ethyl acetate/hexane (0% to 15%) to give the title compound.
Workup
- customfor 4 hours at 100° C. in an oil bath to give crude product which
- customwas purified by silica gel flash chromatography
- washeluting with ethyl acetate/hexane (0% to 15%)
Sources & evidence
- ORD record
- ord-c599ce57f282422c9bbe8afcd7577a43
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353091B2
Reaction notes
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