3-Aminophenylboronic acid → HCID 10237080, compound

HRID 1992308Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][N:16]=[CH:15]3)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1>CC(O)C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:21][C:22]1[CH:27]=[C:26]([C:2]2[N:3]=[C:4]([NH:11][C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][N:16]=[CH:15]4)[C:5]3[S:10][CH:9]=[CH:8][C:6]=3[N:7]=2)[CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-N-(1H-indazol-5-yl)thieno[3,2-d]pyrimidin-4-amine (10 mmol, 1 equivalent) was suspended in dimethyl ethylene glycol (60 mL) and Na2CO3 solution (2M, 10 mL) and flushed with argon for 20 min. To this suspension 3-aminophenyl boronic acid (25 mmol, 2.5 eq) and Pd(PPh3)4 (2.5 mmol, 0.25 eq) were added. The reaction mixture was refluxed under AR at 100° C. for 48 h. The solvent was evaporated off in vacuo. The residue was taken into THF (100 mL) plus EtOAc/water. (100 mL, 1:1). The organic layer was evaporated to dryness. The residue was separated by silica gel column chromatography (0-5% MeOH in CH2Cl2). The product was obtained as yellow powder (2.04 g, 57%). (M+H)+=359, RT (LC-MS)=1.93.

Workup

customNa2CO3 solution (2M, 10 mL) and flushed with argon for 20 min
customThe solvent was evaporated off in vacuo
customThe organic layer was evaporated to dryness
customThe residue was separated by silica gel column chromatography (0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-95c6d21eb1e34b519dcb5b26c37f1678
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648986B2

Reaction notes

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