Sodium Iodide → 2-[4-(3-Pyrrolidin-1-ylpropoxy)phenyl]-2h-indazole

HRID 598785Notes

Reaction equation

[N:1]1[N:2]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2.[I-].[Na+].[H-].[Na+].Cl[CH2:22][CH2:23][CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>CN(C)C=O>[N:25]1([CH2:24][CH2:23][CH2:22][O:16][C:13]2[CH:14]=[CH:15][C:10]([N:2]3[CH:3]=[C:4]4[C:9]([CH:8]=[CH:7][CH:6]=[CH:5]4)=[N:1]3)=[CH:11][CH:12]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 4-Indazol-2-ylphenol (28 mg, 0.13 mmol) and sodium iodide (6 mg, 0.04 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (8.0 mg, 60% in mineral oil, 0.2 mmol) followed by 1-(3-chloropropyl)pyrrolidine (30 mg, 0.20 mmol). After the reaction was heated at 85° C. overnight and allowed to cool, it was partitioned between water and methylene chloride. The organic layer was dried (MgSO4), concentrated and purified by semi-prep LC-MS to give 5.0 mg of the desired indazole. LC-MS (C20H23N3O calc'd 321) m/z 322 (M+H); 1H NMR (300 MHz, CDCl3) δ 8.33 (s, 1H), 7.81-7.77 (m, 3H), 7.71 (d, J=8.7 Hz, 1H), 7.34-7.29 (m, 1H), 7.14-7.09 (m, 1H), 7.05-7.02 (m, 2H), 4.10 (t, J=6.6 Hz, 2H), 2.72 (t, J=7.2 Hz, 2H), 2.63 (m, 4H), 2.08 (quint, J=6.3 Hz, 2H), 1.86-1.81 (m, 4H).

Workup

temperatureto cool
customit was partitioned between water and methylene chloride
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
custompurified by semi-prep LC-MS

Sources & evidence

ORD record: ord-ffb5b2a3c227423296670211f60b8365
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897634B2

Reaction notes

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