4-Chlorophenylboronic acid → 4-chloro-2-(4-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1508819Notes

Reaction equation

HRID 1508819 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:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1>>[Cl:11][C:4]1[CH:3]=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=12

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 903384814-chloro-2-(4-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridineYield 78%

Procedure

Following General Procedure F, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.350 g, 1.86 mmol) was reacted with (4-chlorophenyl)boronic acid (0.378 g, 2.42 mmol) to afford the title compound (0.355 g, 78%). MW=264.15. 1H NMR (CD3OD, 300 MHz) δ 7.96-7.83 (m, 2H), 7.61 (d, J=4.6 Hz, 1H), 7.51-7.39 (m, 2H), 3.13-2.99 (m, 4H), 2.25-2.14 (m, 2H); APCI MS m/z 264 [M+H]+.

Sources & evidence

ORD record
ord-1a7d33b5d4a1482691b1aabd6e167d46
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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