Ethyl 2-aminobenzoate → HCID 57857520, compound

HRID 2266963Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5](CS([O-])(=O)=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:13][C:14]2[CH:24]=[CH:23][CH:22]=[CH:21][C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Following general procedure A, a mixture of 4-fluorophenylmethanesulfonate (95 mg, 0.5 mmol), ethyl 2-aminobenzoate (89 μL, 0.6 mmol), K2CO3 (97 mg, 0.7 mmol), 10 (4 mg, 1 mol %), 1 (2.5 mg, 1 mol %), and t-BuOH (6 mL) was heated to 110° C. for 16 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-20% EtOAc/hexanes) to provide the title compound as a yellow oil (118 mg, 91%). 1H NMR (300 MHz, CDCl3) δ: 9.44 (s, 1H), 7.99 (d, J=8.0 Hz, 1H), 7.30 (t, J=7.5 Hz, 1H), 7.21 (m, 2H), 7.07 (m, 3H), 6.73 (t, J=7.5 Hz, 1H), 4.37 (q, J=7.5 Hz, 2H), 1.42 (t, J=7.5 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 168.8, 161.3, 158.1, 148.8, 136.9, 136.9, 134.4, 131.9, 125.4, 125.3, 117.1, 116.5, 116.2, 113.6, 112.0, 60.9, 14.6 ppm. IR (neat, cm−1): 3316, 2982, 1683, 1583, 1513, 1455, 1260, 1233, 1082, 749. Anal. Calcd. for C15H14FNO2: C, 69.49; H, 5.44. Found: C, 70.14; H, 5.64.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-20% EtOAc/hexanes)

Sources & evidence

ORD record: ord-9601061cafdf450da175ef2ba5ffea45
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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