Water → 6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

HRID 2205863Notes

Reaction equation

CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[C:12]([NH2:14])[C:11]([C:15]#[C:16][C:17]2[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=2)=[CH:10][N:9]=1.[Cl-].[NH4+].O>CN1C(=O)CCC1.CN1C(=O)CCC1.O>[Br:7][C:8]1[N:9]=[CH:10][C:11]2[CH:15]=[C:16]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[NH:14][C:12]=2[CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Potassium t-butoxide (315 mg 2.81 mmole) was dissolved in NMP (3 mL) and 2-bromo-5-((1-methyl-1H-pyrazol-4-yl)ethynyl)pyridin-4-amine (24) (375 mg 1.35 mmole) was added to the stirred solution. The reaction was placed under nitrogen and warmed at 50° C. for 3 hours. The reaction was cooled and 10% ammonium chloride (3 mL) added. Water (21 mL) was heated to about 60° C. and the product solution in NMP/water was added to the water; a solid immediately crashes out. The suspension was allowed to cool to r.t., filtered and the solid washed with water. Drying in a vac desiccator over KOH for 3 days gave product (347 mg) which was azeotroped with ethanol (2×15 mL) and toluene (2×15 mL) to give the title compound (315 mg, 84%). 1H-NMR (d6-DMSO, 500 MHz): δ 3.90 (s, 3H), 6.69 (d, J=0.95 Hz, 1H), 7.47 (t, J=0.95 Hz, 1H), 7.94 (d, J=0.63 Hz, 1H), 8.18 (s, 1H), 8.50 (d, J=0.95 Hz, 1H), 11.92 (br s, 1H, NH).

Workup

temperatureThe reaction was cooled
temperatureto cool to r.t.
filtrationfiltered
washthe solid washed with water
dry with materialDrying in a vac desiccator over KOH for 3 days

Sources & evidence

ORD record: ord-15c42a27c6ea44688746962c9839b892
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371319B2

Reaction notes

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