Potassium Carbonate → HCID 68431906, compound

HRID 2092083Notes

Reaction equation

HRID 2092083 reaction equation
Br[C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[O:11])[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30].[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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]>[CH:31]1([C:2]2[C:7](=[O:8])[N:6]([CH2:9][C:10]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[O:11])[N:5]=[CH:4][C:3]=2[NH:20][C@@H:21]2[CH2:26][C@@H:25]3[CH2:27][C@@H:23]([C:24]3([CH3:29])[CH3:28])[C@H:22]2[CH3:30])[CH2:33][CH2:32]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 68430690HCID 68430690, compound

Product 1

HCID 68431906HCID 68431906, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

2-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)acetamide (62 mg, 0.131 mmol), cyclopropylboronic acid (45 mg, 0.524 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (13 mg, 0.013 mmol) and potassium carbonate (72 mg, 0.524 mmol) in 1,4-dioxane-water (9/1, 0.7 mL) were stirred in a nitrogen stream at 100° C. for 6 hours. After cooling the reaction solution was concentrated, and the resulting residue was purified by silica gel chromatography (chloroform/methanol=8/1) to give the desired product (42 mg, 74% yield).

Workup

  1. temperatureAfter cooling the reaction solution
  2. concentrationwas concentrated
  3. customthe resulting residue was purified by silica gel chromatography (chloroform/methanol=8/1)

Sources & evidence

ORD record
ord-23b5ee3de36845c692e9a6b87662cacb
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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