Potassium Carbonate → HCID 86706325, compound

HRID 2205937Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:10][C:4]=2[CH:3]=1.Br[C:18]1[N:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.C(OCC)(=O)C.[Cu]I>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:10]([C:18]3[N:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 210 °C

Procedure

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 27 mg 0.10 mmole) and 2-bromopyrimidine (24 mg, 0.15 mmole) were dissolved in DMA (0.7 ml) and potassium carbonate (20 mg, 0.14 mmole) and copper(I) iodide (4.0 mg, 0.022 mmole) were added. The reaction was placed under argon and heated by microwave at 210° C. for 60 minutes. The reaction was taken up in ethyl acetate (25 mL) and the solution washed with water (3×7 mL) and brine. The combined organic layers were dried and concentrated in vacuo. The residue was purified using preparative TLC eluting with ethyl acetate to afford the title compound (31 mg). 1H-NMR (CDCl3, 500 MHz): 3.95 (s, 3H), 6.73 (d, J=0.95 Hz), 7.34 (s, 1H) under 7.34 (t, J=5.04 Hz, 1H), 7.53 (s, 1H), 8.11 (t, J=0.95 Hz, 1H), 8.66 (d, J=0.95 Hz, 1H), 8.85 (d, J=5.04 Hz, 2H),

Workup

washthe solution washed with water (3×7 mL) and brine
customThe combined organic layers were dried
concentrationconcentrated in vacuo
customThe residue was purified
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-0f6ec1575ef4494f81833172a162f6ee
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371319B2

Reaction notes

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