Sodium Iodide → Methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 1400689Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:23]=[C:11]3[N:12]=[C:13]([CH3:22])[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:15](Cl)[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[Na+].[I-:25]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:23]=[C:11]3[N:12]=[C:13]([CH3:22])[C:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])=[C:15]([I:25])[N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-(2-(3-bromophenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1 g, 2.53 mmol) and NaI (1.519 g, 10.14 mmol) were suspended in acetonitrile (10 mL) and the resulting mixture was heated at 80° C. for 5 h. After cooling to room temp, mixture was diluted with ethyl acetate (50 mL) and washed with water (25 mL) and aqueous Na2S2O3 (25 mL), dried (Na2SO4), filtered and concentrated. Crude was then triturated with ethyl acetate/hexane to afford methyl 2-(2-(3-bromophenyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (1 g, 2.057 mmol, 81% yield) as off white solid. 1H NMR (400 MHz, CDCl3) δ: 8.20 (t, J=1.8 Hz, 1H), 7.95 (dt, J=7.8, 1.3 Hz, 1H), 7.55 (ddd, J=8.0, 2.0, 1.0 Hz, 1H), 7.36 (t, J=7.9 Hz, 1H), 7.08 (s, 1H), 4.02 (s, 2H), 3.79 (s, 3H), 2.66 (s, 3H). LCMS (M+H)=486.1.

Workup

temperatureAfter cooling to room temp
washwashed with water (25 mL) and aqueous Na2S2O3 (25 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customCrude was then triturated with ethyl acetate/hexane

Sources & evidence

ORD record: ord-0ddc1b89aaad42a2b3ff94342c6d0d0a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906929B2

Reaction notes

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