7-Amino-4-bromo-2-methylisoindolin-1-one → 7-amino-4-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-methyl-2,3-dihydro-1H-isoindol-1-one

Participants

Role	Name	HCID	Charge
Reactant	7-Amino-4-bromo-2-methylisoindolin-1-one	HCID 53408459	—
Reactant	4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-ol	HCID 67814792	—
Reactant	2-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide	HCID 86697680	—
Product	7-amino-4-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-methyl-2,3-dihydro-1H-isoindol-1-one	HCID 86697710	22%

Reaction Steps

Prepared analogously to Compound 3C using 7-amino-4-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one (Compound 17D, 300 mg, 1.24 mmol) and 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-ol (Compound 14C, 364 mg, 1.37 mmol) to afford 81 mg of the title compound (22%). 1H NMR (400 MHz, CDCl3) d 7.65 (s, 1H), 7.50 (s, 1H), 7.36 (d, J=8.3 Hz, 1H), 6.63 (d, J=8.3 Hz, 1H), 5.25 (br. s., 2H), 4.38 (s, 2H), 4.23 (t, J=7.0 Hz, 2H), 3.70 (t, J=6.2 Hz, 2H), 3.18 (s, 3H), 1.98-2.08 (m, 2H), 1.60-1.66 (m, 2H) [OH obscured].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133224B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-ddc1499e53184a35bc385bbec909381c
Source note	uspto-grants-2015_09