3-Tolylboronic acid → HCID 118037184, compound

HRID 1508836Notes

Reaction equation

HRID 1508836 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.B(O)(O)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1>>[ClH:1].[Cl:11][C:4]1[CH:3]=[C:2]([C:13]2[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=12

Participants

3

Reactant 2

HCID 27339503-Tolylboronic acidHCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 118037184HCID 118037184, compoundYield 82%

Procedure

Following General Procedure F, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.300 g, 1.60 mmol) was reacted with 3-tolyboronic acid (0.282 g, 2.07 mmol), followed by the formation of the hydrochloride salt to afford the title compound (0.244 g, 82%) as a white solid. MW=280.19. 1H NMR (CDCl3, 500 MHz) δ 13.97 (s, 1H), 7.97 (s, 1H), 7.91 (d, J=7.5 Hz, 1H), 7.74 (s, 1H), 7.49 (t, J=7.5 Hz, 1H), 7.41 (d, J=7.5 Hz, 1H), 3.84 (t, J=7.6 Hz, 2H), 3.15 (t, J=7.6 Hz, 2H), 2.49 (s, 3H), 2.41-2.37 (m, 2H); APCI MS m/z 244 [M+H]+.

Sources & evidence

ORD record
ord-08df0bf1b7ec459d8502881d1380b009
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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