Ethyl Acetate → HCID 58754806, compound

HRID 1711234Notes

Reaction equation

HRID 1711234 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11](B3OCC(C)(C)CO3)[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[N:25]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Br[C:40]1[CH:41]=[CH:42][C:43]([NH2:46])=[N:44][CH:45]=1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.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>[NH2:46][C:43]1[N:44]=[CH:45][C:40]([C:11]2[CH:10]=[CH:9][C:8]([NH:21][C:22]([C:24]3[N:25]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:37])[CH3:38])[CH:26]=[C:27]([C:29]#[N:30])[N:28]=3)=[O:23])=[C:7]([C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=3)[CH:12]=2)=[CH:41][CH:42]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 58754872HCID 58754872, compound

Product 1

HCID 58754806HCID 58754806, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-amide (as prepared in the previous step, 32.0 mg, 0.0600 mmol), 5-bromo-pyridin-2-ylamine (10.4 mg, 0.0660 mmol) and Pd(PPh3)4 (7.0 mg, 0.0060 mmol) in 1.0 mL of 1,4-dioxane was added 2.0 M Na2CO3 aqueous solution (0.24 mL, 0.48 mmol). The resulting mixture was stirred at 80. C for 6 h under Ar. After cooling to RT, the mixture was treated with 30 mL of EtOAc, washed with H2O (3×15 mL) and brine (10 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (2-3% MeOH/DCM) to afford 24 mg (78%) of the title compound as a white solid: Mass spectrum (ESI, m/z): Calcd. for C28H34N6O2Si, 515.3 (M+H), found 515.2.

Workup

  1. washwashed with H2O (3×15 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel (2-3% MeOH/DCM)

Sources & evidence

ORD record
ord-8722a227d8af4dd5b924e3d7c4f234fc
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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