Ethanol → 6-bromo-1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid amide

HRID 1025636Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[N:28]=[CH:27][C:26]5[C:21](=[C:22]([F:33])[CH:23]=[C:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:25]=5)[C:20]4=[O:34])[C:14]=3[CH2:35][OH:36])[CH:9]=[C:10]([C:11]#[N:12])[C:5]2=[CH:4][CH:3]=1.C([OH:39])C>O>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[N:28]=[CH:27][C:26]5[C:21](=[C:22]([F:33])[CH:23]=[C:24]([C:29]([CH3:31])([CH3:32])[CH3:30])[CH:25]=5)[C:20]4=[O:34])[C:14]=3[CH2:35][OH:36])[CH:9]=[C:10]([C:11]([NH2:12])=[O:39])[C:5]2=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

In a 25 mL round-bottomed flask, 6-bromo-1-(3-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-2-(hydroxymethyl)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (14 mg, 25.6 μmol) and [hydrogen bis(dimethylphosphinito-kP)]platinum (II) (110 μg, 0.256 μmol, Eq: 0.01) were combined with Ethanol (2.99 ml) and Water (2.99 ml) to give a colorless solution. The reaction mixture was heated to 45° C. and stirred for 1 h. The crude reaction mixture was concentrated in vacuo. Purification by HPLC gave 6-bromo-1-[3-(6-tert-butyl-8-fluoro-1-oxo-1H-phthalazin-2-yl)-2-hydroxymethyl-phenyl]-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid amide (11 mg, 77%, [M+H]+ 565).

Workup

customto give a colorless solution
customThe crude reaction mixture
concentrationwas concentrated in vacuo
customPurification by HPLC

Sources & evidence

ORD record: ord-b1d4b36f00c648308f9b3ee4936a52ad
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729078B2

Reaction notes

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