(Cyclopent-1-en-1-yl)boronic acid → HCID 90112155, compound

HRID 1508840Notes

Reaction equation

HRID 1508840 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]CC)=[O:17])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:21]([F:24])([F:23])[F:22])[N:3]=1.[C:25]1(B(O)O)[CH2:29][CH2:28][CH2:27][CH:26]=1>>[C:25]1([C:2]2[CH:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=3)[CH:5]=[C:4]([C:21]([F:23])([F:24])[F:22])[N:3]=2)[CH2:29][CH2:28][CH2:27][CH:26]=1

Participants

3

Reactant 2

HCID 3861343(Cyclopent-1-en-1-yl)boronic acidHCID 90113032HCID 90113032, compound

Product 1

HCID 90112155HCID 90112155, compoundYield 24.1%

Procedure

Following General Procedure F, ethyl 2-(4-((2-chloro-6-(trifluoromethyl)pyridin-4-yl)amino)phenyl)acetate (0.115 g, 0.32 mmol) was reacted with cyclopent-1-en-1-ylboronic acid (0.039 g, 0.35 mmol) to afford the title compound (0.028 g, 24%) as a yellow oil. MW=362.35. 1H NMR (CDCl3, 500 MHz) 8.7.35-7.28 (m, 2H), 7.18-7.11 (m, 2H), 7.02-6.95 (m, 1H), 6.89 (s, 1H), 6.69-6.63 (m, 1H), 6.18 (s, 1H), 3.65 (s, 3H), 2.05 (q, J=7.5 Hz, 4H), 1.30-1.22 (m, 2H); APCI MS m/z 363 [M+H]+.

Sources & evidence

ORD record
ord-613ae6108bb049e78944fe214cf5df8b
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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