Sodium Carbonate → HCID 68893881, compound

HRID 1821041Notes

Reaction equation

HRID 1821041 reaction equation
Br[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][C:8]=2[CH3:22])=[N:5][N:6]=1.[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[F:31])#[N:24].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[C:23]([C:25]1[CH:26]=[C:27]([N:6]2[N:5]=[C:4]([C:7]3[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][C:8]=3[CH3:22])[S:3][CH2:2]2)[CH:28]=[CH:29][C:30]=1[F:31])#[N:24]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27579643-Cyano-4-fluorophenylboronic acidHCID 68888320HCID 68888320, compound

Product 1

HCID 68893881HCID 68893881, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 3-(4-(2-Bromo-1,3,4-thiadiazol-5-yl)-3-methylphenyl)propenoate (0.15 g, 0.39 mmol, from Step A), 3-cyano-4-fluorophenyl boronic acid (0.097 g, 0.59 mmol, from Step B) and sodium carbonate (0.21 g, 1.95 mmol) were dissolved in DMF (6 mL) and water (0.2 mL). The reaction mixture was degassed for 5 min with a balloon of argon after which tetrakis(triphenylphosphine) palladium (0.1 g) was added. The reaction was heated at 80° C. for 3 h. The reaction was diluted with water and extracted with ethyl acetate (2×100 mL). The combined organics were dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 10% ethyl acetate/hexane afforded 0.05 g of product: ESI-MS (m/z) 422.2; HPLC A: 4.21 min.

Workup

  1. customThe reaction mixture was degassed for 5 min with a balloon of argon after which tetrakis(triphenylphosphine) palladium (0.1 g)
  2. additionwas added
  3. additionThe reaction was diluted with water
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washSilica gel chromatography eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a87c902e32524356a09891c96262fa7c
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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