Potassium Phosphate, Tribasic → HCID 57502368, compound

HRID 2070884Notes

Reaction equation

ClC1C2C(=CC=C([C:12]3[N:17]4[N:18]=[C:19]([NH:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[N:20]=[C:16]4[CH:15]=[CH:14][CH:13]=3)C=2)C=CN=1.ClC1C2C(=CC=C(B(O)O)C=2)C=CN=1.BrC1N2N=C(NC3C=CC=CC=3)N=C2C=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O>[C:22]1([NH:21][C:19]2[N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][N:17]3[N:18]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 90 °C

Procedure

5-(1-Chloroisoquinolin-7-yl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-amine. A degassed mixture of 1-chloroisoquinolin-7-ylboronic acid (288 mg, 1.38 mmol), 5-bromo-N-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-amine (400 mg, 1.38 mmol), potassium phosphate (296 mg, 2.76 mmol) and tetrakis (triphenylphosphine)palladium(0) (160 mg, 0.138 mmol) in dimethylsulfoxide (10 mL) was heated at 90° C. under nitrogen overnight. After being cooled down to room temperature, the reaction mixture was filtered, and the filtrate was concentrated in vacuo to give the crude product, which was washed with ethyl acetate to give 541-chloroisoquinolin-7-yl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridine-2-amine (200 mg, 38.7% yield) as a solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm) 9.68 (br s, 1H), 9.23 (s, 1H), 8.45 (d, J=8.4 Hz, 1H), 8.41 (d, J=5.2 Hz, 1H), 8.27 (d, J=8.8 Hz, 1H), 8.01 (d, J=5.6 Hz, 1H), 7.69 (m, 4H), 7.44 (d, J=6.0 Hz, 1H), 7.23 (t, J=7.6 Hz, 2H), 6.85 (t, J=7.2 Hz, 1H); MS (ESI) m/z: 372.1 [M+1].+

Workup

temperatureAfter being cooled down to room temperature
filtrationthe reaction mixture was filtered
concentrationthe filtrate was concentrated in vacuo
customto give the crude product, which
washwas washed with ethyl acetate

Sources & evidence

ORD record: ord-ebf0831eef284050ae28b41dd7b2f47c
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299056B2

Reaction notes

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