4-bromo-1-methyl-1H-pyrrole-2-carboxylic acid amide → 4-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amide

HRID 1025566Notes

Reaction equation

HRID 1025566 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=[O:9])[N:5]([CH3:7])[CH:6]=1.[C:11]([C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([F:25])[CH:24]=1)[C:21](=[O:26])[N:20]([C:27]1[CH:37]=[CH:36][CH:35]=[C:34](B3OC(C)(C)C(C)(C)O3)[C:28]=1[CH2:29][O:30]C(=O)C)[N:19]=[CH:18]2)([CH3:14])([CH3:13])[CH3:12]>>[C:11]([C:15]1[CH:16]=[C:17]2[C:22](=[C:23]([F:25])[CH:24]=1)[C:21](=[O:26])[N:20]([C:27]1[C:28]([CH2:29][OH:30])=[C:34]([C:2]3[CH:3]=[C:4]([C:8]([NH2:10])=[O:9])[N:5]([CH3:7])[CH:6]=3)[CH:35]=[CH:36][CH:37]=1)[N:19]=[CH:18]2)([CH3:14])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 434111534-bromo-1-methyl-1H-pyrrole-2-carboxylic acid amideHCID 594737692-(6-(tert-Butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate2×

Product 1

HCID 710082674-[3-(6-tert-Butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amideYield 60%

Procedure

This compound was prepared with the same method as described in Example 1 by using 4-bromo-1-methyl-1H-pyrrole-2-carboxylic acid amide (intermediate-3) and acetic acid 2-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (intermediate 5). The desired compound was prepared in two steps (60% yield). 1H NMR (300 MHz, d6-DMSO) δ 8.49-8.48 (m, 1H), 7.86 (s, 1H), 7.73 (d, J=13.2 Hz, 1H), 7.44-7.42 (m, 3H), 7.25-7.23 (m, 2H), 7.06 (br s, 2H), 4.56 (s, 1H), 4.36 (s, 2H), 3.88 (s, 3H), 1.37 (s, 9H). LC-MS calcd for C25H25FN4O3 (m/e) 448.19, obsd 449.1 [M+H]+.

Workup

  1. customThis compound was prepared with the same method

Sources & evidence

ORD record
ord-6b157db2efd34f51be2dc2c3bbe7fb57
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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