Sodium hydride → HCID 9938746, compound

HRID 1358749Notes

Reaction equation

HRID 1358749 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([N:13]2[C:17]([OH:18])=[CH:16][C:15]([C:19]([O:21][CH3:22])=[O:20])=[N:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].[N+:27]([C:30]1[CH:35]=[C:34]([S:36]([C:39]([F:42])([F:41])[F:40])(=[O:38])=[O:37])[CH:33]=[CH:32][C:31]=1Cl)([O-:29])=[O:28]>>[CH3:22][O:21][C:19]([C:15]1[CH:16]=[C:17]([O:18][C:31]2[CH:32]=[CH:33][C:34]([S:36]([C:39]([F:41])([F:42])[F:40])(=[O:38])=[O:37])=[CH:35][C:30]=2[N+:27]([O-:29])=[O:28])[N:13]([C:5]2[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=2)[N:14]=1)=[O:20]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzeneHCID 178498590HCID 178498590, compound

Product 1

HCID 9938746HCID 9938746, compound

Procedure

Using procedure as in example 10, a reaction of methyl 1-[3,5-di(trifluoromethyl)phenyl]-5-hydroxy-1H-pyrazole-3-carboxylate (100 mg, 0.282 mmol), NaH (12 mg, 1.1 equiv.) and 2-nitro-4-(trifluoromethylsulfonyl)chlorobenzene (82 mg, 1 equiv.) afforded 1-(3,5-bis-trifluoromethyl-phenyl)-5-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-1H-pyrazole-3-carboxylic acidmethyl ester. 1HNMR (300 MHz, DMSO-d6) δ 8.76 (d, J=2.1 Hz, 1H), 8.58 (dd, J=2.1 & 8.2 Hz, 1H), 8.42 (s, 2H), 8.30 (s, 1H), 8.13 (d, J=8.2 Hz, 1H), 6.76 (m, 1H), 3.7 (s, 3H, OCH3). MS-EI m/z 607 [M+].

Sources & evidence

ORD record
ord-63a56e7f038e4198b7cc1538b5178994
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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