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Potassium Phosphate, Tribasic → HCID 66599721, compound

HRID 1909059
Notes
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Reaction equation

HRID 1909059 reaction equation
Br[C:2]1[C:6]([CH3:7])=[N:5][N:4]2[CH2:8][CH2:9][CH2:10][C:3]=12.[CH3:11][O:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CCOC(C)=O.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>[CH3:11][O:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[C:16]([C:2]2[C:6]([CH3:7])=[N:5][N:4]3[CH2:8][CH2:9][CH2:10][C:3]=23)[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 56973105Methyl 4-cyano-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 665994623-bromo-2-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

Product 1

HCID 66599721HCID 66599721, compoundYield 49.8%

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

In a pressure sealed flask a suspension of 3-bromo-2-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (1.01 g, 5.0 mmol), 4-cyano-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (1.8 g, 6.25 mmol), and K3PO4 (2.65 g, 12.5 mmol) in dioxane (50 mL) was degassed by bubbling N2 for 30 m at room temperature. After the addition of tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol) the reaction flask was sealed and the contents heated to 95° C. for 5 h. After cooling the reaction mixture was diluted several fold with EtOAc, and washed with dilute aqueous NaHCO3 followed by brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified over normal phase silica starting with 100% DCM for 5 m and then increasing to 10% MeOH in DCM over 25 m to give the desired product as a yellow solid (0.70 g, 2.49 mmol). MS m/z 282.5 (M+H)+.

Workup

  1. customIn a pressure sealed flask
  2. customwas degassed
  3. customby bubbling N2 for 30 m at room temperature
  4. customwas sealed
  5. temperatureAfter cooling the reaction mixture
  6. washwashed with dilute aqueous NaHCO3
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified over normal phase silica starting with 100% DCM for 5 m
  11. temperatureincreasing to 10% MeOH in DCM over 25 m

Sources & evidence

ORD record
ord-a8d1a4bf7a174430a7e8c8bf3fb78fca
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598217B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes