Dichloromethane → 6-(4-Fluorophenylamino)phthalazin-1-ol

HRID 454862Notes

Reaction equation

HRID 454862 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[N:7][N:6]=[CH:5]2.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.C(Cl)Cl.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>CC1CCCO1.CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([OH:12])=[N:7][N:6]=[CH:5]3)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 97314-FluoroanilineHCID 2733832Lithium HexamethyldisilazideHCID 178518884HCID 178518884, compound

Product 1

HCID 1785189066-(4-Fluorophenylamino)phthalazin-1-ol

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolventHCID 73012-MethyltetrahydrofuranSolvent

Procedure

A mixture of 6-bromophthalazin-1-ol (1.00 g, 4.44 mmol), 4-fluorobenzenamine (0.642 g, 5.78 mmol), Pd(dppf)Cl2.CH2Cl2 (0.130 g, 0.178 mmol), and lithium bis(trimethylsilyl)amide (2.23 g, 13.3 mmol) in 2-methyltetrahydrofuran (10 mL) was heated at 95° C. in an oil bath for 24 h in a sealed tube. The mixture was cooled to RT, diluted with MeOH and filtered through a pad of Celite. The filtrate was concentrated over silica gel. The residue was purified using column chromatography (0-4% MeOH in CH2Cl2) to yield the title compound as a yellow crystalline solid. MS (ESI, pos. ion) m/z: 256.0 (M+1).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated over silica gel
  3. customThe residue was purified

Sources & evidence

ORD record
ord-c80fc78b1a544d2187cd9205e15bca72
Source dataset
uspto-grants-2013_07
Patent number
US08497269B2

Reaction notes

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