5-Chlorothiophene-2-boronic acid → HCID 90338494, compound

HRID 1508969Notes

Reaction equation

HRID 1508969 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[S:17][C:16](B(O)O)=[CH:15][CH:14]=1>>[Cl:11][C:4]1[CH:3]=[C:2]([C:16]2[S:17][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 27343245-Chlorothiophene-2-boronic acidHCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 90338494HCID 90338494, compoundYield 14.3%

Procedure

Following general procedure F, 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.150 g, 0.80 mmol) was reacted with (5-chlorothiophen-2-yl)boronic acid (0.142 g, 0.88 mmol) to afford the title compound (0.031 g, 14%) as a white solid. MW=270.18. 1H NMR (CDCl3, 500 MHz) δ 7.32 (s, 1H), 7.27 (d, J=4.0 Hz, 1H), 6.89 (d, J=4.0 Hz, 1H), 3.08 (t, J=7.5 Hz, 2H), 2.98 (t, J=7.5 Hz, 2H), 2.16 (quin, J=7.5 Hz, 2H); APCI MS m/z 270 [M+H]+.

Sources & evidence

ORD record
ord-8865a2b6000d40d9a0c7df31fe7493c9
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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