Dimethylformamide → HCID 86711680, compound

HRID 710656Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:25])[CH2:18][N:19]4[CH:23]=[C:22](I)[CH:21]=[N:20]4)[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][N:27](C=O)C>[C-]#N.[C-]#N.[Zn+2].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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:26]([C:22]1[CH:21]=[N:20][N:19]([CH2:18][C:17]([N:12]2[CH2:13][CH2:14][CH2:15][C:16]3[N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[N:9]=[CH:10][C:11]2=3)=[O:25])[CH:23]=1)#[N:27]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-(4-iodopyrazol-1-yl)ethanone (0.388 g, 0.86 mmol), Zn(CN)2 (0.151 g, 1.29 mmol), Pd2(dba)3 (0.079 g, 0.086 mmol) and dppf (0.072 g, 0.13 mmol) in DMF (10 mL) was heated at 90° C. for 1 hr. It was then cooled to rt. The mixture was partitioned between EtOAc (10 mL) and sat. NaHCO3 (50 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography with a gradient elution of 0-100% EtOAc/CH2Cl2 to afford 2-(4-cyanopyrazol-1-yl)-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone (0.205 g, 68%).

Workup

temperatureIt was then cooled to rt
customThe mixture was partitioned between EtOAc (10 mL) and sat. NaHCO3 (50 mL)
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified by flash chromatography with a gradient elution of 0-100% EtOAc/CH2Cl2

Sources & evidence

ORD record: ord-1664379e196741fab855f6d259641fba
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181241B2

Reaction notes

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