Tricyclohexylphosphine → 6-(6-Methylpyrazin-2-yl)-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine

HRID 57884

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[N:11]=[CH:10][C:9]2[CH:12]=[N:13][N:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[C:8]=2[CH:7]=1)CCC.Cl[C:30]1[CH:35]=[N:34][CH:33]=[C:32]([CH3:36])[N:31]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CN(C)C(=O)C.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]>[CH3:36][C:32]1[N:31]=[C:30]([C:6]2[N:11]=[CH:10][C:9]3[CH:12]=[N:13][N:14]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][O:16]4)[C:8]=3[CH:7]=2)[CH:35]=[N:34][CH:33]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of tributyl-(1-tetrahydropyran-2-ylpyrazolo[4,3-c]pyridin-6-yl)stannane (7.139 mmol; 3514.5 mg), 2-chloro-6-methyl-pyrazine (10.71 mmol; 1377 mg), tricyclohexylphosphine; (0.5140 mmol; 144.1 mg) and tris(dibenzylideneacetone)dipalladium (0) (0.2142 mmol; 196.1 mg) in N,N-Dimethylacetamide (15 mL) was purged with Argon for 1 min. The reaction mixture was sealed in a pressure vial and heated at 130° C. overnight. The mixture was partitioned between EtOAc and water. The organic layer was concentrated and the residue was purified on silica eluted with 0 to 100% EtOAc in DCM to afford 6-(6-methylpyrazin-2-yl)-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine as a clear oil (1.3608 g, 60%).

Workup

customThe reaction mixture was sealed in a pressure vial
customThe mixture was partitioned between EtOAc and water
concentrationThe organic layer was concentrated
customthe residue was purified on silica
washeluted with 0 to 100% EtOAc in DCM

Sources & evidence

ORD record: ord-81aad0fd0aaf44388e143b3bd8f47840
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434725B2

Linked notes

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