2,5-Dimethylaniline → HCID 57857515, compound

HRID 2266962Notes

Reaction equation

[N:1]1([C:6]2[CH:11]=[CH:10][C:9](CS([O-])(=O)=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH3:17][C:18]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:19]=1[NH2:20].C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:20][C:19]3[CH:21]=[C:22]([CH3:25])[CH:23]=[CH:24][C:18]=3[CH3:17])=[CH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5]1

Participants

Conditions

Temperature: 110 °C

Procedure

Following general procedure A, a mixture of 4-(1H-pyrrol-1-yl)phenylmethanesulfonate (119 mg, 0.5 mmol), 2,5-dimethylaniline (75 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; 0-30% EtOAc/hexanes) to provide the title compound as a white solid (138 mg, 95%), mp 97-98° C. 1H NMR (300 MHz, CDCl3) δ: 7.31 (d, J=9.0 Hz, 2H), 7.14 (d, J=7.5 Hz, 1H), 7.04 (m, 5H), 6.82 (d, J=7.5 Hz, 1H), 6.37 (t, J=2.5 Hz, 2H), 5.40 (s, 1H), 2.33 (s, 3H), 2.27 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 142.4, 141.1, 136.9, 134.4, 131.2, 125.6, 123.3, 122.3, 119.9, 119.8, 118.5, 110.0, 21.5, 17.8 ppm. IR (neat, cm−1): 3386, 2920, 1519, 1310, 1072, 829, 726. Anal. Calcd. for C18H18N2: C, 82.41; H, 6.92. Found: C, 82.03; H, 7.03.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-4cd2e314e92b401c9af03b6a603df0b7
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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