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

HRID 1025563Notes

Reaction equation

HRID 1025563 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](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C:26]1[CH:36]=[CH:35][CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[C:27]=1[CH2:28][O:29]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](=[CH:23][CH:24]=1)[C:21](=[O:25])[N:20]([C:26]1[C:27]([CH2:28][OH:29])=[C:33]([C:2]3[CH:3]=[C:4]([C:8]([NH2:10])=[O:9])[N:5]([CH3:7])[CH:6]=3)[CH:34]=[CH:35][CH:36]=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 580162042-(6-tert-butyl-1-oxophthalazin-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate2×

Product 1

HCID 710085174-[3-(6-tert-Butyl-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1-methyl-1H-pyrrole-2-carboxylic acid amideYield 20%

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-1-oxo-1H-phthalazin-2-yl)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl ester (intermediate 4). The desired compound was prepared in two steps (20% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.54 (s, 1H), 8.25 (d, J=8.4 Hz, 1H), 8.04 (d, J=1.5 Hz, 1H), 8.01 (dd, J=1.8, 8.4 Hz, 1H), 7.48-7.45 (m, 2H), 7.28-7.23 (m, 2H), 7.08 (d, J=1.8 Hz, 1H), 4.35 (s, 2H), 3.89 (s, 3H), 1.41 (s, 9H). LC-MS calcd for C25H26N4O3 (m/e) 430.20, obsd 431 [M+1]+.

Workup

  1. customThis compound was prepared with the same method

Sources & evidence

ORD record
ord-2d9d09ba69b842548c6f0501cc6b537d
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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