Bromide ion → HCID 58486878, compound

HRID 2272248Notes

Reaction equation

HRID 2272248 reaction equation
[Br-].FC1(F)OC2C=C(C)C(C3N=[CH:14][C:15]([NH:18][C:19](=O)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4F)=[N:16]C=3)=CC=2O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.[C:44](#N)C.O>>[CH3:39][C:40]1[O:41][C:42]2[CH:43]=[CH:21][CH:22]=[CH:23][C:24]=2[C:25]=1[C:20]1[CH:44]=[CH:14][C:15]([NH2:16])=[N:18][CH:19]=1

Participants

5

Reactant 4

HCID 259Bromide ionHCID 62657Potassium Phosphate, TribasicHCID 58486754N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamideHCID 67448433Dioxane acetonitrile water

Product 1

HCID 58486878HCID 58486878, compoundYield 76%

Conditions

Temperature
90 °C

Procedure

Palladium tetrakis-triphenylphosphine (68 mg, 0.1 mmol) was added to a degassed solution of bromide 244 (250 mg, 1.2 mmol) and boronate 11 (521 mg, 2.4 mmol) in dioxane: acetonitrile:water (9:9:2, 6 mL) and potassium phosphate (376 mg, 1.8 mmol). The resulting mixture was heated under argon at 90° C. with stiffing for 18 hours. The mixture was then cooled, extracted with dichloromethane (3×15 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 245 (202 mg, 76%) as an solid: LRESIMS m/z 225.2 [M+H]+, calcd. for C14H13N2O1 225.1.

Workup

  1. temperatureThe mixture was then cooled
  2. extractionextracted with dichloromethane (3×15 mL)
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3d027ff7cd7e4cf0b9de3242a764583e
Source dataset
uspto-grants-2015_09
Patent number
US09120751B2

Reaction notes

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