Dimethylformamide → 4-Chloro-3-hydroxy-5-fluoro-2-(1-methyl-1-phenylethyl)isoindolinone

HRID 21240Notes

Reaction equation

HRID 21240 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[C:5]([NH:7][C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])=[O:6].CN(CCN(C)C)C.CN([CH:32]=[O:33])C>C1COCC1>[Cl:1][C:2]1[C:19]([F:20])=[CH:18][CH:17]=[C:4]2[C:3]=1[CH:32]([OH:33])[N:7]([C:8]([CH3:16])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])[C:5]2=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 684919423-chloro-4-fluoro-N-(1-methyl-1-phenylethyl)benzamide

Product 1

HCID 684908724-Chloro-3-hydroxy-5-fluoro-2-(1-methyl-1-phenylethyl)isoindolinoneYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a similar manner to Step 2 of Example 16, 3-chloro-4-fluoro-N-(1-methyl-1-phenylethyl)benzamide (3.00 g, 10.3 mmol) was dissolved in THF (120 mL), and the solution was treated with TMEDA (5.00 mL, 32.9 mmol), sec-butyl lithium-hexane solution (1.01 mol/L, 32.6 mL, 32.9 mmol) and DMF (1.80 mL, 22.6 mmol), followed by purification by flash column chromatography (chloroform) and by slurry (chloroform) to obtain 4-chloro-3-hydroxy-5-fluoro-2-(1-methyl-1-phenylethyl)isoindolinone (1.50 g, yield 46%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform) and by slurry (chloroform)

Sources & evidence

ORD record
ord-34ca4dfef10c4f44a1e018b2a412f6e0
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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