Ammonia → HCID 9861493, compound

HRID 891272Notes

Reaction equation

HRID 891272 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12](Br)=[C:11]([O:16][CH3:17])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.[F-].[Cs+].N>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)=[C:11]([O:16][CH3:17])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25953Cesium fluorideHCID 2856454-Fluorophenylboronic acidHCID 21934054HCID 21934054, compound

Product 1

HCID 9861493HCID 9861493, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-benzyl-5-methoxy-4-bromo-3(2H)-pyridazinone, prepared according to the method of (S. Cho et al. described in J. Het. Chem., (1996), 33, 1579-1582), (2.94 g; 10 mmol), 4-fluorobenzeneboronic acid (1.54 g; 11 mmol), and CsF (3.04 g; 22 mmol) in 25 mL of anhydrous DME, under N2, was added Pd(Ph3P)4 (347 mg 0.3 mmol). After addition, the mixture was heated at reflux for at 100° C., for 18 hours. The mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and water. The acetate layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The solid residue was suspended in ethyl ether-hexanes and filtered to provide a solid product (yield: 3.1 g; about 100%; >95% purity). 1H NMR (300 MHz, CDCl3) δ 3.90 (s, 3H), 5.36 (s, 2H), 7.09 (t, J=9 Hz, 2H), 7.31 (m, 3H), 7.50 (m, 4H), 7.91 (s, 1H). MS (DCI/NH3) m/z 311 (M+H)+, 328 (M+NH4)+.

Workup

  1. customprepared
  2. additionAfter addition
  3. temperaturethe mixture was heated
  4. concentrationThe mixture was concentrated in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. washThe acetate layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. filtrationfiltered
  10. customto provide a solid product (yield: 3.1 g; about 100%; >95% purity)

Sources & evidence

ORD record
ord-26ef8fb8f2cf4d87bb3091f78eab7783
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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