1-Cyclohexenylboronic acid → HCID 90338623, compound

HRID 1508976Notes

Reaction equation

HRID 1508976 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)[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=1>>[Cl:11][C:4]1[CH:3]=[C:2]([C:12]2[CH2:17][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 38629021-Cyclohexenylboronic acidHCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 90338623HCID 90338623, compoundYield 66.2%

Procedure

Following general procedure F, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.157 g, 0.84 mmol) was reacted with cyclohex-1-en-1-ylboronic acid (0.142 g, 1.13 mmol) to afford crude product (0.130 g) as an oil. MW=233.74. 1H NMR (CDCl3, 500 MHz) δ 7.13 (s, 1H), 7.08 (s, 1H), 6.70-6.66 (m, 1H), 3.06 (t, J=7.5 Hz, 2H), 2.96 (t, J=7.5 Hz, 2H), 2.47-2.42 (m, 2H), 2.27-2.22 (m, 2H), 2.17-2.09 (m, 2H), 1.82-1.75 (m, 2H), 1.69-1.63 (m, 2H); APCI MS m/z 234 [M+H]+.

Sources & evidence

ORD record
ord-4cdf0ccf2f7643f1970b876a49f84f4e
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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