(2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl acetate → HCID 86684084, compound

HRID 407823Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[N:14][N:13]([CH:16]([F:18])[F:17])[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[C:19]([O:22][CH2:23][C:24]1[C:25]([N:39]2[N:48]=[CH:47][C:46]3[C:41](=[C:42]([F:53])[CH:43]=[C:44]([C:49]([CH3:52])([CH3:51])[CH3:50])[CH:45]=3)[C:40]2=[O:54])=[N:26][CH:27]=[CH:28][C:29]=1B1OC(C)(C)C(C)(C)O1)(=[O:21])[CH3:20]>>[C:19]([O:22][CH2:23][C:24]1[C:25]([N:39]2[N:48]=[CH:47][C:46]3[C:41](=[C:42]([F:53])[CH:43]=[C:44]([C:49]([CH3:51])([CH3:50])[CH3:52])[CH:45]=3)[C:40]2=[O:54])=[N:26][CH:27]=[CH:28][C:29]=1[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:15]=[N:14][N:13]([CH:16]([F:18])[F:17])[N:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1)(=[O:21])[CH3:20]

Participants

Reactant 2

HCID 86683972(2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)methyl acetate

HCID 86684083HCID 86684083, compound

Product 1

HCID 86684084HCID 86684084, compoundYield 32.1%

Procedure

Following the procedure of Example 152c, and starting with 159c (150 mg, 0.46 mmol, 1.0 eq.) and 3-(acetoxymethyl)-2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)pyridin-4-ylboronic acid (116c) (285 mg, 0.69 mmol, 1.5 eq.) afforded 159d as a yellow solid (90 mg, 32%). MS-ESI:[M+H]+ 609.3

Sources & evidence

ORD record: ord-c16d74b82d5c4f079982df16232f70af
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754077B2

Reaction notes

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