Ethyl 2-(4-amino-2-fluorophenyl)acetate → HCID 118037428, compound

HRID 1508756Notes

Reaction equation

HRID 1508756 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[N:5]=[C:4]2[CH2:15][CH2:16][CH2:17][C:3]=12.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([F:31])[CH:20]=1>>[Cl:14][C:10]1[CH:9]=[C:8]([C:6]2[N:5]=[C:4]3[CH2:15][CH2:16][CH2:17][C:3]3=[C:2]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:21]([F:31])[CH:20]=3)[CH:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 15840528Ethyl 2-(4-amino-2-fluorophenyl)acetateHCID 901106754-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine

Product 1

HCID 118037428HCID 118037428, compoundYield 94%

Procedure

Following General Procedure B2, 4-chloro-2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridine (0.100 g, 0.33 mmol) was reacted with ethyl 2-(4-amino-2-fluorophenyl)acetate (0.098 g, 0.50 mmol) to afford the title compound (0.094 g, 94%). MW=424.90. 1H NMR (CD3OD, 300 MHz) δ 7.79-7.75 (m, 1H), 7.66-7.60 (m, 1H), 7.45-7.36 (m, 2H), 7.30 (t, J=8.4 Hz, 1H), 7.20 (s, 1H), 7.11-7.05 (m, 1H), 7.04-6.97 (m, 1H), 4.17 (q, J=7.1 Hz, 2H), 3.68 (s, 2H), 3.02 (t, J=7.6 Hz, 2H), 2.89 (t, J=7.6 Hz, 2H), 2.30-2.13 (m, 2H), 1.26 (t, J=7.6 Hz, 3H); APCI MS m/z 425 [M+H]+.

Sources & evidence

ORD record
ord-e2b4c1d959f24973aee42ccf2eff1ff5
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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