(3-Acetamidophenyl)boronic acid → HCID 44250429, compound

HRID 1409138Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[CH:3]=1.[C:24]([NH:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:26])[CH3:25]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:24]([NH:27][C:28]1[CH:33]=[C:32]([C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([NH:11][C:12](=[O:23])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[CH:3]=2)[CH:31]=[CH:30][CH:29]=1)(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 1.0 equivalent), 3-acetamidophenylboronic acid (2.0 equivalents), and PdCl2(dppf) (0.08 equivalent) in 1:2 saturated NaHCO3/dioxane (0.15 M with respect to 2D) was heated at 110° C. for 15 minutes in the microwave. After cooling to room temperature, the crude mixture was filtered and the filtrate was purified by preparatory LC-MS to give the titled compound (35%) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6H) 2.09 (s, 3H) 5.20 (s, 1H) 6.60 (d, J=2.27 Hz, 1H) 7.52-7.57 (m, 1H) 7.60-7.64 (m, 2H) 7.73-7.77 (m, 1H) 7.84-7.89 (m, 1H) 7.99-8.07 (m, 2H) 8.20 (d, J=2.27 Hz, 1H) 8.28 (t, J=1.77 Hz, 1H) 10.24 (s, 1H) 11.28 (s, 1H). ESI-MS: m/z 430.3 (M+H)+.

Workup

temperatureAfter cooling to room temperature
filtrationthe crude mixture was filtered
customthe filtrate was purified by preparatory LC-MS

Sources & evidence

ORD record: ord-480a2444f6274bc0b8028fdee0691bdf
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921358B2

Reaction notes

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