Sodium Chloride → HCID 25204729, compound

HRID 515572Notes

Reaction equation

HRID 515572 reaction equation
Br[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:15][CH2:14][CH:13]([N:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[CH2:12][CH2:11]3)=[N:6][N:5]2[C:21]=1[C:22]1[CH:27]=[CH:26][N:25]=[N:24][CH:23]=1.[F:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[C:33]([F:35])[CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>O1CCOCC1.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].C(OCC)(=O)C>[F:28][C:29]1[CH:30]=[C:31]([C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][C:7]([N:10]4[CH2:15][CH2:14][CH:13]([N:16]5[CH2:20][CH2:19][CH2:18][CH2:17]5)[CH2:12][CH2:11]4)=[N:6][N:5]3[C:21]=2[C:22]2[CH:27]=[CH:26][N:25]=[N:24][CH:23]=2)[CH:32]=[C:33]([F:35])[CH:34]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 59367710HCID 59367710, compound

Product 1

HCID 25204729HCID 25204729, compoundYield 38.2%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.090 g (0.21 mmol) of 2-bromo-3-pyridazin-4-yl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)imidazo[1,2-b]pyridazine, 0.014 g (0.02 mmol) of 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium and 0.043 g (0.27 mmol) of 3,5-difluorophenylboronic acid and of a 2M aqueous solution of cesium carbonate in 2 ml of dioxane is heated at 120° C. for 20 minutes in a microwave oven. 1 ml of a saturated aqueous solution of sodium chloride and 4 ml of ethyl acetate are then injected into the tube. After stirring, the organic phase is removed with a syringe and passed over a sodium sulfate cartridge. The solution is directly injected onto a silica gel column and chromatographed, elution being carried out with a mixture of 0 to 10% of methanol in dichloromethane. 0.037 g of product is thus isolated.

Workup

  1. customthe organic phase is removed with a syringe
  2. customchromatographed
  3. washelution
  4. additionbeing carried out with a mixture of 0 to 10% of methanol in dichloromethane

Sources & evidence

ORD record
ord-04d9c2c9865f477aa781d5f785d9cbd6
Source dataset
uspto-grants-2015_08
Patent number
US09108971B2

Reaction notes

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