Potassium Phosphate, Tribasic → HCID 59548528, compound

HRID 1879682Notes

Reaction equation

HRID 1879682 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:13]=1.[CH:14]1(B(O)O)[CH2:16][CH2:15]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:14]1([C:2]2[CH:3]=[CH:4][C:5]3[C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][C:6]=3[CH:13]=2)[CH2:16][CH2:15]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 59548554HCID 59548554, compound

Product 1

HCID 59548528HCID 59548528, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-Bromo-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (1.02 g, 4.23 mmol, 1 eq), cyclopropylboronic acid (480 mg, 5.5 mmol, 1.3 eq), tricyclohexylphosphine (121 mg, 0.42 mmol, 0.1 eq), Pd(OAc)2 (48 mg, 0.211 mmol, 0.05 eq), K3PO4 (3.2 g, 14.8 mmol, 3.5 eq) in Toluene (40 mL), water (4 mL), dioxane (10 mL), was degassed with argon and heated to 110 C for 15 hours. The reaction was cooled, diluted with ethyl acetate, washed sat. aq. Sodium bicarbonate solution, brine, and dried over mgso4, filtered, concentrated in vacuo and purified with flash chromatography on a silica gel column eluting with 50% ethyl acetate in hexanes to give 650 mg 8-Cyclopropyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one, 76%.

Workup

  1. customwas degassed with argon
  2. temperatureheated to 110 C for 15 hours
  3. temperatureThe reaction was cooled
  4. additiondiluted with ethyl acetate
  5. washwashed sat. aq. Sodium bicarbonate solution, brine
  6. customdried over mgso4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified with flash chromatography on a silica gel column
  10. washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b1f7acfe5cdb447b9735ff1f37aeb066
Source dataset
uspto-grants-2012_11
Patent number
US08318719B2

Reaction notes

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