Phenol → HCID 117737149, compound

HRID 1504531Notes

Reaction equation

HRID 1504531 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([NH:22][C:23]4[CH:27]=[CH:26][O:25][N:24]=4)(=[O:21])=[O:20])=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:28])=[C:4]([O:29][CH2:30][C:31]#[N:32])[CH:3]=1.Br[CH:34](C)C#N.C1(O)C=CC=CC=1>>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([S:19]([NH:22][C:23]4[CH:27]=[CH:26][O:25][N:24]=4)(=[O:20])=[O:21])=[CH:16][CH:17]=3)[CH:12]=[CH:11][C:10]2=[O:28])=[C:4]([O:29][CH:30]([C:31]#[N:32])[CH3:34])[CH:3]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 1405382-BromopropionitrileHCID 117737018HCID 117737018, compound

Product 1

HCID 117737149HCID 117737149, compoundYield 14%

Procedure

This compound was made in an analogous fashion to 1-(4-bromo-2-(cyanomethoxy)-5-fluorophenyl)-N-(isoxazol-3-yl)-2-oxo-1,2-dihydroquinoline-6-sulfonamide via Method 166 except employing 2-bromopropanenitrile in the first step to alkylate the phenol. The yield of the desired product after HPLC purification was 5.3 mgs (14% yield). 1H NMR (500 MHz, DMSO-d6) □=ppm 1.36 (d, J=6.62 Hz, 2 H) 3.02-3.11 (m, 1 H) 3.17 (s, 1 H) 5.43-5.51 (m, 1 H) 6.16-6.22 (m, 1 H) 6.72 (d, J=9.73 Hz, 2 H) 7.67-7.78 (m, 2 H) 7.84-7.94 (m, 1 H) 8.15-8.24 (m, 2 H) 8.35 (br. s., 1 H). m/z (ESI) 530.9 (M−H).

Workup

  1. customThe yield of the desired product after HPLC purification

Sources & evidence

ORD record
ord-45d9d09cbe9e4a9ab10474ba0949226a
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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