2-(Tributylstannyl)pyridine → 4-Chloro-7-fluoro-2-(pyridin-2-yl)quinoline-3-carbonitrile

HRID 1618572Notes

Reaction equation

Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]([Cl:14])[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][CH:8]=2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)CCC>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C1(C)C=CC=CC=1>[Cl:14][C:10]1[C:9]2[C:4](=[CH:5][C:6]([F:15])=[CH:7][CH:8]=2)[N:3]=[C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:11]=1[C:12]#[N:13]

Participants

Conditions

Temperature: 100 °C

Procedure

Prepared according to procedure E using 2,4-dichloro-7-fluoroquinoline-3-carbonitrile (230 mg, 0.95 mmol) (described herein), 2-(tributylstannyl)pyridine (0.42 mL, 1.15 mmol), tetrakis(triphenylphosphine)palladium(o) (110 mg, 0.095 mmol), and toluene (4.1 mL). The reaction mixture was stirred at 100° C. for 18 h, and subsequent purification afforded 4-chloro-7-fluoro-2-(pyridin-2-yl)quinoline-3-carbonitrile as an off-white solid. Mass Spectrum (ESI) m/e=284 (M+1).

Workup

customPrepared
customsubsequent purification

Sources & evidence

ORD record: ord-952fe90eb1e14c98b557c4963ced8f5b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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