Toluene → HCID 66635827, compound

HRID 872100Notes

Reaction equation

HRID 872100 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]3[N:15]=[C:16]([CH3:19])[C:17](I)=[C:13]3[N:12]=[C:11]([N:20]3[CH2:24][CH2:23][CH2:22][C@H:21]3[CH2:25][OH:26])[CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:27]1[O:35][C:34]2[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][C:29]=2[O:28]1.C1(C)C=CC=CC=1.C([O-])(O)=O.[Na+]>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.C(O)C>[CH2:27]1[O:35][C:34]2[CH:33]=[CH:32][C:31]([C:17]3[C:16]([CH3:19])=[N:15][N:14]4[C:9]([C:4]5[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=5)=[CH:10][C:11]([N:20]5[CH2:24][CH2:23][CH2:22][C@H:21]5[CH2:25][OH:26])=[N:12][C:13]=34)=[CH:30][C:29]=2[O:28]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 66635660HCID 66635660, compound

Product 1

HCID 66635827HCID 66635827, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

(S)-(1-(7-(3,5-Difluorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)methanol (40 mg), 3,4-methylenedioxyphenylboronic acid (23 mg) and tetrakis(triphenylphosphine)palladium (10 mg) are added to toluene (5 mL), ethanol (3 mL) and 1 N NaHCO3 aqueous solution (1.5 mL) and stirred at 85° C. for 4 hours under argon atmosphere. After cooling to room temperature, the reaction solvent is removed by distillation under reduced pressure. The remainder is extracted with ethyl acetate and water. The organic layer is washed with brine and dehydrated with anhydrous MgSO4. The dehydrated organic layer is concentrated by distillation under reduced pressure and purified by column chromatography to yield the target compound (36 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction solvent is removed by distillation under reduced pressure
  3. extractionThe remainder is extracted with ethyl acetate and water
  4. washThe organic layer is washed with brine
  5. concentrationThe dehydrated organic layer is concentrated by distillation under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-cd8eb8d167b34d84bb7cca31441bc4ea
Source dataset
uspto-grants-2015_03
Patent number
US08975264B2

Reaction notes

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