4-Bromoanisole → HCID 59612403, compound

HRID 1889826Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

Reactant 2

HCID 77304-Bromoanisole

HCID 674790495-(4-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 59612403HCID 59612403, compoundYield 11%

Procedure

[5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-methoxy-phenyl)-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (115 mg, 0.40 mmol) and p-bromoanisole (82 mg, 0.44 mmol) in a manner analogous to Example 77 to yield [5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-methoxy-phenyl)-amine (17 mg, 11%) as a yellow powder following purification on a 12 g Isco silica gel column using methanol in dichloromethane (0-10%) as eluent. MP=229° C. (dec.). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.43 (s, 1H), 8.32 (d, J=7.50 Hz, 2H), 8.14 (d, J=7.50 Hz, 2H), 7.54-7.71 (m, 4H), 7.27 (d, J=6.4 Hz, 1H), 6.87 (d, J=7.5 Hz, 2H), 3.71 (s, 3H), 3.34 (s, 3H). MS=395 (MH)+.

Sources & evidence

ORD record: ord-a4ea16dd67ee4a6fad46605ab72b0d67
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501936B2

Reaction notes

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