Ethyl Acetate → HCID 86713608, compound

HRID 2274236Notes

Reaction equation

HRID 2274236 reaction equation
I[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]#[N:12])[C:5]2=[N:4][CH:3]=1.[CH:13]([O:16][C:17]1[CH:18]=[C:19]([NH:32][C:33]([NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[O:34])[CH:20]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:22]=1)([CH3:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.[Cl-].[Na+].O>[C:11]([C:10]1[C:5]2[N:6]([C:2]([C:21]3[CH:20]=[C:19]([NH:32][C:33]([NH:35][CH2:36][C:37]([F:38])([F:39])[F:40])=[O:34])[CH:18]=[C:17]([O:16][CH:13]([CH3:15])[CH3:14])[CH:22]=3)=[CH:3][N:4]=2)[CH:7]=[CH:8][CH:9]=1)#[N:12]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 58081529HCID 58081529, compoundHCID 717572643-Iodo-imidazo[1,2-a]pyridine-8-carbonitrile

Product 1

HCID 86713608HCID 86713608, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 3-iodoimidazo[1,2-a]pyridine-8-carbonitrile (100 mg, 373 μmol), 1-(3-isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea (90 mg, 224 μmol), PdCl2(dppf)-CH2Cl2Adduct (30.5 mg, 37.3 μmol) in Dioxane (3 ml), was added 2M Na2CO3 (0.559 ml, 1119 μmol). The vial was degassed for 5 minutes then capped and heated to 110° C. for 30 minutes in microwave. After cooling to ambient temperature reaction was partioned between EtOAc and brine, separated and organics washed with brinex2. Combined organics were dried directly on to silica and purified via flash chromatography (0-100% Hex/EtOAc; 12 g column). Recovered the title compound (30 mg, 71.9 μmol, 32.1% yield) as a brown solid. MS (ES+) C20H18F3N5O2 requires: 417. Found: 418 [M+H]+.

Workup

  1. customThe vial was degassed for 5 minutes
  2. customthen capped
  3. temperatureAfter cooling to ambient temperature
  4. customreaction
  5. customseparated
  6. washorganics washed with brinex2
  7. customCombined organics were dried directly on to silica
  8. custompurified via flash chromatography (0-100% Hex/EtOAc; 12 g column)

Sources & evidence

ORD record
ord-d6f77d342339496ba0f86ea3000a1605
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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