Potassium Carbonate → 2-[4-(1-Tritylpyrazolo[5,4-b]pyridin-4-yl)pyrazol-1-yl]acetonitrile

HRID 44680Notes

Reaction equation

[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[CH:10][N:9]=[C:8]3[N:12]([C:15]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:13]=[CH:14][C:7]=23)[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][C:42]#[N:43].[Cl-].[Na+].O.CCOC(C)=O>C1COCC1>[C:15]([N:12]1[C:8]2=[N:9][CH:10]=[CH:11][C:6]([C:4]3[CH:5]=[N:1][N:2]([CH2:41][C:42]#[N:43])[CH:3]=3)=[C:7]2[CH:14]=[N:13]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-(1H-pyrazol-4-yl)-1-trityl-pyrazolo[5,4-b]pyridine (3.824 g, 8.945 mmol) and potassium carbonate (9.890 g, 71.56 mmol) in dry THF (100.0 mL) was treated with 2-bromoacetonitrile (8.583 g, 4.984 mL, 71.56 mmol) and heated at 90° C. for 5 hours. The reaction was allowed to cool and treated with brine/ EtOAc and the 2 layers separated. The combined organics were dried (MgSO4), filtered, concentrated and purified by column chromatography (1:1 Petroleum ether/EtOAc) to give a white solid on concentration. The material was taken forward to the next step. 1H NMR (CDCl3, 400 MHz) δ 5.21 (2H, s), 7.06 (1H, s), 7.27-7.28 (15H, m), 8.04 (2H, m), 8.25 (2H, m); MS (ES+) 467.19

Workup

temperatureto cool
customthe 2 layers separated
dry with materialThe combined organics were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
custompurified by column chromatography (1:1 Petroleum ether/EtOAc)
customto give a white solid
concentrationon concentration

Sources & evidence

ORD record: ord-408f71a40f8b44bda4871fc88d96f1f8
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541445B2

Reaction notes

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