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

HRID 2279722Notes

Reaction equation

HRID 2279722 reaction equation
NC1C=CC(C2C=NN(CCCO)C=2)=CC=1C(N(CC)CC)=O.Br[C:25]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[C:30]2[C:26]=1[CH2:27][N:28]([CH3:38])[C:29]2=[O:37].CC1(C)C(C)(C)OB(C2C=NN(CCCO)C=2)O1.[CH3:57][C:58]1([CH3:78])[O:62][C@@H:61]([CH2:63][N:64]2[CH:68]=[C:67](B3OC(C)(C)C(C)(C)O3)[CH:66]=[N:65]2)[CH2:60][O:59]1>>[CH3:57][C:58]1([CH3:78])[O:62][C@@H:61]([CH2:63][N:64]2[CH:68]=[C:67]([C:25]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[C:30]4[C:26]=3[CH2:27][N:28]([CH3:38])[C:29]4=[O:37])[CH:66]=[N:65]2)[CH2:60][O:59]1

Participants

5

Reactant 4

HCID 534078944-Bromo-2-methyl-7-nitroisoindolin-1-oneHCID 671871273-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-1-olHCID 67253006(S)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×HCID 866976802-amino-N,N-diethyl-5-[1-(3-hydroxypropyl)-1H-pyrazol-4-yl]benzamide

Product 1

HCID 67811915HCID 67811915, compoundYield 99%

Procedure

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).

Sources & evidence

ORD record
ord-8fa34322c2ab427c953f7f1bde675534
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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