Triethylamine → 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-3-[(5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)ethynyl]pyrazolo[1,5-a]pyridine

HRID 1253475Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[C:10]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[CH:9]=[C:8]([O:18][CH3:19])[C:7]=12)#[CH:2].I[C:21]1[CH:22]=[N:23][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[C:25]=1[CH3:26].C(N(CC)CC)C>CN(C)C=O.[Cu]I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:19][O:18][C:8]1[C:7]2[N:6]([N:5]=[CH:4][C:3]=2[C:1]#[C:2][C:21]2[CH:22]=[N:23][N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:25]=2[CH3:26])[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)[CH:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 3-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (30.0 mg, 0.12 mmol), 2-(4-iodo-5-methyl-1H-pyrazol-1-yl)pyridine (51.0 mg, 0.18 mmol), copper (I) iodide (6.8 mg, 0.036 mmol), and tetrakis(triphenylphosphine)palladium (0) (14 mg, 0.012 mmol) in N,N-dimethylformamide (2 ml), was added triethylamine (0.033 ml, 0.24 mmol). The mixture was sparged with argon for 3 minutes and heated to 60° C. After 1 h, reaction mixture was purified directly by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give 4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)-3-[(5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)ethynyl]pyrazolo[1,5-a]pyridine.

Workup

customThe mixture was sparged with argon for 3 minutes
customreaction mixture
customwas purified directly by preparative HPLC Reverse phase (C-18)
washeluting with acetonitrile/water+0.05% TFA

Sources & evidence

ORD record: ord-0771019d723d40ff8337be25157b4239
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455477B2

Reaction notes

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