3-(Methylsulfonyl)aniline hydrochloride → 4-(2-Methoxyphenyl)-N-(3-(methylsulfonyl)phenyl)pyridin-2-amine

HRID 593285Notes

Reaction equation

HRID 593285 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH:5]=[CH:4][N:3]=1.Cl.[CH3:17][S:18]([C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)[NH2:24])(=[O:20])=[O:19].COC1C=CC=CC=1C1C=CN=C(NC2C=CC=C([N+]([O-])=O)C=2)C=1>>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:21]([S:18]([CH3:17])(=[O:20])=[O:19])[CH:22]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 27351793-(Methylsulfonyl)aniline hydrochlorideHCID 584326112-Chloro-4-(2-methoxyphenyl)pyridineHCID 601965414-(2-methoxyphenyl)-N-(3-nitrophenyl)pyridin-2-amine

Product 1

HCID 601970494-(2-Methoxyphenyl)-N-(3-(methylsulfonyl)phenyl)pyridin-2-amine

Procedure

F1 was prepared from A1 (281 mg, 1.28 mmol) and 3-(methylsulfonyl)aniline hydrochloride (267 mg, 1.28 mmol) following the procedure reported for C1. Yield: 210 mg (46%). 1H NMR (400 MHz, d6-DMSO, 300K) δ 3.18 (s, 3H), 3.80 (s, 3H), 7.02-7.08 (m, 2H), 7.12-7.18 (m, 2H), 7.35-7.45 (m, 2H), 7.50-7.53 (m, 1H), 7.53-7.62 (m, 1H), 7.92 (d, J=8.0 Hz, 1H), 8.12-8.19 (m, 2H), 10.05 (bs, 1H). MS (ES) C19H18N2O3S requires: 354. found: 355 (M+H)+.

Sources & evidence

ORD record
ord-30532291b7f243e48e4ae8e33168c8e0
Source dataset
uspto-grants-2016_01
Patent number
US09242937B2

Reaction notes

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