4-Bromo-2-methyl-7-nitroisoindolin-1-one → HCID 67811915, compound

Participants

Role	Name	HCID	Charge
Reactant	4-Bromo-2-methyl-7-nitroisoindolin-1-one	HCID 53407894	—
Reactant	3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-ol	HCID 67187127	—
Reactant	(S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 67253006	—
Reactant	2-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide	HCID 86697680	—
Product	HCID 67811915	HCID 67811915	99%

Reaction Steps

Prepared analogously to Compound 3C replacing Compound 3D with Compound 1L and Compound 3E with 1-{[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 5E) to afford 1.96 g of the desired product (99%). 1H NMR (400 MHz, CDCl3) δ 7.79-7.85 (m, 2H), 7.74-7.80 (m, 1H), 7.65-7.73 (m, 1H), 4.46-4.58 (m, 3H), 4.36 (dd, J=5.05, 13.39 Hz, 2H), 4.14 (dd, J=6.44, 8.72 Hz, 1H), 3.83 (dd, J=6.06, 8.59 Hz, 1H), 3.24 (s, 3H), 1.34-1.44 (m, 6H). MS (ESI): m/z 373.16 [M+H]+. UPLC: tR=1.16 min (UPLC-TOF: polar—3 min).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133224B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-8fa34322c2ab427c953f7f1bde675534
Source note	uspto-grants-2015_09