(Cyclopent-1-en-1-yl)boronic acid → HCID 90338499, compound

HRID 1508972Notes

Reaction equation

HRID 1508972 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.[C:12]1(B(O)O)[CH2:16][CH2:15][CH2:14][CH:13]=1>>[Cl:11][C:4]1[CH:3]=[C:2]([C:12]2[CH2:16][CH2:15][CH2:14][CH:13]=2)[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=12

Participants

3

Reactant 2

HCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 90338499HCID 90338499, compoundYield 65%

Conditions

Temperature
140 °C

Procedure

Following general procedure F except the reaction was heated to 140° C. under microwave irradiation for 2 h, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.157 g, 0.84 mmol) was reacted with cyclopent-1-en-1-ylboronic acid (0.112 g, 1.0 mmol) to afford the title compound (0.120 g, 65%) as a white solid. MW=219.71. 1H NMR (CDCl3, 500 MHz) δ 7.06 (s, 1H), 6.62-6.57 (m, 1H), 3.06 (t, J=7.5 Hz, 2H), 2.97 (t, J=7.5 Hz, 2H), 2.77-2.70 (m, 2H), 2.58-2.52 (m, 2H), 2.13 (quin, J=7.5 Hz, 2H), 2.08-2.00 (m, 2H); APCI MS m/z 220 [M+H]+.

Sources & evidence

ORD record
ord-d3c0d8c1e496477c928304c26aee5894
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

Loading…