Potassium Carbonate → 3-Mppts

HRID 392390Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([NH:12][CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:9]=[CH:10][CH:11]=1.[F:24][C:25]([F:32])([F:31])[CH2:26][S:27](Cl)(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([N:12]([CH2:13][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[S:27]([CH2:26][C:25]([F:32])([F:31])[F:24])(=[O:29])=[O:28])[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 5 °C

Procedure

The resultant N-(3-(2-methoxyphenoxy)phenyl)pyrid-3-ylmethylamine was dissolved in 2:1 1,2-dichloroethane/pyridine (6 mL) under nitrogen, cooled (5° C.), and treated with 2,2,2-trifluoroethylsulfonyl chloride (300 mg, 1.64 mmol). After one hour at 5° C., the mixture was allowed to warm to room temperature and stirred for 18 h. The product mixture was treated with anhydrous potassium carbonate (500 mg), stirred 30 min, filtered, and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel (eluted with 2:1 dichloromethane/ethyl acetate) to afford the title compound (226 mg, 50%) as a viscous pale amber oil. The hydrochloride salt was obtained by treatment of this material in methanol with ethereal HCl. 1H NMR: 8.49 (d,1H,J=4 Hz), 8.29 (s,1H), 7.60-7.65 (m,1H), 7.20-7.25 (m,2H), 7.10-7.20 (m,1H), 6.97 (d,1H,J=8 Hz), 6.90 (m,2H), 6.80-6.85 (m,2H), 6.76 (m,1H), 4.82 (s,2H), 3.70-3.85 (m,2H), 3.75 (s,3H). MS calcd. 452.4; MS (M+1) 453.3

Workup

temperatureto warm to room temperature
stirringstirred 30 min
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
customThe residue was chromatographed on silica gel (eluted with 2:1 dichloromethane/ethyl acetate)

Sources & evidence

ORD record: ord-e43d0ba112114d7cb53766689933d0b0
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800651B2

Reaction notes

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