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

HRID 2279754Notes

Reaction equation

HRID 2279754 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][N:18]([CH2:20][CH2:21][CH2:22]O)[CH:19]=2)=[CH:11][C:3]=1[C:4]([N:6]([CH2:9]C)[CH2:7]C)=[O:5].NC1C=CC(Br)=C2C=1[C:32](=[O:34])N(C)C2.CC1(C)C(C)(C)OB(C2C=NN(CCCCO)C=2)O1>>[NH2:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][N:18]([CH2:20][CH2:21][CH2:22][CH2:32][OH:34])[CH:19]=2)=[C:11]2[C:3]=1[C:4](=[O:5])[N:6]([CH3:7])[CH2:9]2

Participants

4

Reactant 3

HCID 534084597-Amino-4-bromo-2-methylisoindolin-1-one2×HCID 678147924-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butan-1-olHCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 866977107-amino-4-[1-(4-hydroxybutyl)-1H-pyrazol-4-yl]-2-methyl-2,3-dihydro-1H-isoindol-1-oneYield 22%

Procedure

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].

Sources & evidence

ORD record
ord-ddc1499e53184a35bc385bbec909381c
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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