3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride) → 4-chloro-2-(3-chloro4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

HRID 1508822Notes

Reaction equation

HRID 1508822 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]=[CH:17][C:18]=1[F:19]>C1(C)C=CC=CC=1.C(O)C.O>[Cl:11][C:4]1[CH:3]=[C:2]([C:15]2[CH:16]=[CH:17][C:18]([F:19])=[C:13]([Cl:12])[CH:14]=2)[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=12

Participants

4

Reactant 2

HCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 903386714-chloro-2-(3-chloro4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridineYield 96%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

Following General Procedure F, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.300 g, 1.60 mmol) in toluene/ethanol/water (6 mL:3 mL:1 mL) was reacted with (3-chloro-4-fluorophenyl)boronic acid (0.362 g, 2.07 mmol) to afford the title compound (0.289 g, 96%) as a white solid. MW=282.14. 1H NMR (CD3OD, 300 MHz) δ 8.15-8.07 (m, 1H), 7.94-7.86 (m, 1H), 7.66 (s, 1H), 7.33 (t, J=8.8 Hz, 1H), 3.12 (t, J=7.6 Hz, 2H), 3.04 (t, J=7.6 Hz, 2H), 2.21 (quin, J=7.6 Hz, 2H); APCI MS m/z 282 [M+H]+.

Sources & evidence

ORD record
ord-b5a7053647c84cf0aefcccc53bd62ee5
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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