Phenylboronic Acid → HCID 68431857, compound

HRID 2092082Notes

Reaction equation

HRID 2092082 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].[C:31]1(B(O)O)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(=O)([O-])[O-].[Na+].[Na+].C(O)CC.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>[C: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])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 68430690HCID 68430690, compound

Product 1

HCID 68431857HCID 68431857, compoundYield 121.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86647509HCID 86647509, compoundSolvent

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 (50 mg, 0.105 mmol), phenylboronic acid (26 mg, 0.21 mmol) and tetrakistriphenylphosphinepalladium (13 mg, 0.011 mmol) in 2 M aqueous sodium carbonate-1-propanol (1:5, 2.4 mL) were stirred in a nitrogen stream at 100° C. overnight. After cooling, the reaction solution was concentrated, and the resulting residue was purified by silica gel chromatography (chloroform/methanol=20/1) to give the desired product (60 mg, 100% yield).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction solution was concentrated
  3. customthe resulting residue was purified by silica gel chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-1341a1a1870e4663bfc851761cdea51c
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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