Sodium hydride → 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-5-(4-methylpentylamino)-4H-1-benzopyran-4-one

HRID 1736179Notes

Reaction equation

HRID 1736179 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:26])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([F:25])[CH:13]=3)[O:11][C:6]=2[C:5]([F:27])=[C:4]([CH3:28])[C:3]=1[F:29].[H-].[Na+].Br[CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37]>>[F:29][C:3]1[C:4]([CH3:28])=[C:5]([F:27])[C:6]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([F:25])[CH:13]=3)=[CH:9][C:8](=[O:26])[C:7]=2[C:2]=1[NH:1][CH2:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 69385Pentane, 1-bromo-4-methyl-HCID 194349955-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-one

Product 1

HCID 194347866,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-5-(4-methylpentylamino)-4H-1-benzopyran-4-oneYield 58%

Procedure

Substantially the same manner as that in Example 114 (1) was repeated except that 1.02 g (2.54 mmol) of 5-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-4H-1-benzopyran-4-one obtained in Example 107 (1), 306 mg (7.65 mmol) of sodium hydride (60% oil dispersion) and 0.90 mL (6.3 mmol) of 1-bromo-4-methylpentane were used under argon atmosphere, to give 718 mg of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-methyl-5-(4-methylpentylamino)-4H-1-benzopyran-4-one (yield: 58%).

Sources & evidence

ORD record
ord-7b05c13f10354652b1a3015e6623cda5
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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