2,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine → 4-chloro-2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1508825Notes

Reaction equation

HRID 1508825 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[C:17]([F:19])[CH:18]=1>>[Cl:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:16]=[C:17]([F:19])[CH:18]=[C:13]([Cl:12])[CH:14]=2)[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=12

Participants

3

Reactant 2

HCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridineHCID 15391287(3-Chloro-5-fluorophenyl)boronic acid

Product 1

HCID 901122754-chloro-2-(3-chloro-5-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridineYield 90%

Procedure

Following General Procedure F, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.250 g, 1.33 mmol) was reacted with (3-chloro-5-fluorophenyl)boronic acid (0.301 g, 2.07 mmol), to afford the title compound (0.224 g, 90%) as a white solid. MW=282.14. 1H NMR (CD3OD, 300 MHz) δ 7.87-7.84 (m, 1H), 7.72-7.65 (m, 2H), 7.30-7.21 (m, 1H), 3.17-3.00 (m, 4H), 2.21 (quin, J=7.6 Hz, 2H); APCI MS m/z 282 [M+H]+.

Sources & evidence

ORD record
ord-a7358a1380de4d43a9303bdacc94ab43
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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