Sodium Carbonate → HCID 46178810, compound

HRID 2096575Notes

Reaction equation

HRID 2096575 reaction equation
[NH2:1][C:2]1[N:3]([CH3:20])[C:4](=[O:19])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[O:9][C:8]([CH3:18])([CH3:17])[CH2:7]2)[N:6]=1.[C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)#[N:22].C([O-])([O-])=O.[Na+].[Na+]>CC1C=CC=CC=1C.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>[NH2:1][C:2]1[N:3]([CH3:20])[C:4](=[O:19])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:27]4[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=4)[C:21]#[N:22])[CH:14]=3)[O:9][C:8]([CH3:18])([CH3:17])[CH2:7]2)[N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 58423762HCID 58423762, compound

Product 1

HCID 46178810HCID 46178810, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
90 °C

Procedure

Pd(PPh3)4 (15.13 mg, 0.013 mmol) is added to the solution of 2′-amino-6-bromo-1′,2,2-trimethylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (44.15 mg, 0.13 mmol) and 3-cyanophenylboronic acid (19.25 mg, 0.13 mmol) in dimethyl-benzene (5 mL) and an aqueous solution of Na2CO3 (2 M, 0.24 mL). The mixture is heated at 90° C. in an oil bath overnight. The mixture is concentrated to give the crude product, which is purified by preparative TLC to give the desired product 3-(2′-amino-1′,2,2-trimethyl-5′-oxo-1′,5′-dihydrospiro[chroman-4,4′-imidazole]-6-yl)benzonitrile (10 mg, 15%).

Workup

  1. concentrationThe mixture is concentrated
  2. customto give the crude product, which
  3. customis purified by preparative TLC

Sources & evidence

ORD record
ord-ae6960c503da4b9aa42357bb7b8d8220
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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