(+-)-2-Butanol → B-[2-[4-[(4-Phenyl-1-phthalazinyl)amino]phenoxy]-3-pyridinyl]boronic acid

HRID 911202Notes

Reaction equation

[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[C:12]([B:13]([OH:15])[OH:14])=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:21][N:20]=1.CC(O)CC>CCCCCC>[C:29]1([C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]([NH:1][C:2]3[CH:17]=[CH:16][C:5]([O:6][C:7]4[C:12]([B:13]([OH:15])[OH:14])=[CH:11][CH:10]=[CH:9][N:8]=4)=[CH:4][CH:3]=3)=[N:20][N:21]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-(4-Aminophenoxy)pyridin-3-ylboronic acid (478 mg, 2.08 mmol), 1-chloro-4-phenylphthalazine (500 mg, 2.08 mmol) and butan-2-ol (4.16 ml, 2.08 mmol) were placed in a sealed tube. The reaction vessel was sealed and the mixture heated to 100° C. After 1 h 45 min, the reaction was cooled to rt. Hexane was added and the precipitated tan solid was filtered off with hexanes. LCMS of the solids indicated product, 2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-ylboronic acid. MS Calculated for C25H19BN4O: [M]+=434. Found: [M+1]+=435.

Workup

customThe reaction vessel was sealed
temperaturethe reaction was cooled to rt
filtrationthe precipitated tan solid was filtered off with hexanes

Sources & evidence

ORD record: ord-ba3644f0a7fe4a94b59b92dfb787ac95
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022221B2

Reaction notes

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