3-(Bromomethyl)-2-fluoropyridine → 2-{1-[(2-fluoro-3-pyridinyl)methyl]-1H-pyrazol-3-yl}-1H-isoindole-1,3(2H)-dione

HRID 1625076Notes

Reaction equation

HRID 1625076 reaction equation
FC1N=C([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])=[N:10]2)C=CC=1.BrC[C:27]1[C:28]([F:33])=[N:29][CH:30]=[CH:31][CH:32]=1>>[F:33][C:28]1[C:27]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([N:14]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15]3=[O:24])=[N:10]2)=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

3

Reactant 2

HCID 230708853-(Bromomethyl)-2-fluoropyridineHCID 86691612HCID 86691612, compound

Product 1

HCID 682779802-{1-[(2-fluoro-3-pyridinyl)methyl]-1H-pyrazol-3-yl}-1H-isoindole-1,3(2H)-dioneYield 62.3%

Procedure

Title compound was prepared by a method analogous to that described for Intermediate 45, replacing 2-(chloromethyl)-6-fluoropyridine with Intermediate 13 (200 mg, 1.051 mmol) to yield the title compound (211 mg, 0.655 mmol, 62.3% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 8.21 (m, 1H), 8.00 (d, 1H), 7.95-7.88 (m, 4H), 7.78 (m, 1H), 7.38 (m, 1H), 6.41 (d, 1H), 5.46 (s, 2H). [ES+MS] m/z 323 (MH+).

Workup

  1. customTitle compound was prepared by a method analogous to

Sources & evidence

ORD record
ord-995c5d2e379746bcb29281a2927a46ab
Source dataset
uspto-grants-2014_07
Patent number
US08779153B2

Reaction notes

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