Potassium Phosphate, Tribasic → HCID 178419889, compound

HRID 1695696Notes

Reaction equation

HRID 1695696 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([NH:10][C@H:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][CH2:12]3)[O:8][CH2:9][C:4]=2[CH:3]=1.[CH:22]1(B(O)O)[CH2:24][CH2:23]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.[Pd].O>[CH:22]1([C:2]2[CH:21]=[CH:20][C:5]3[N:6]=[C:7]([NH:10][C@H:11]4[C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[CH2:13][CH2:12]4)[O:8][CH2:9][C:4]=3[CH:3]=2)[CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 178419299HCID 178419299, compound

Product 1

HCID 178419889HCID 178419889, compoundYield 45.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A stirred mixture of (6-bromo-4H-benzo[d][1,3]oxazin-2-yl)-(R)-indan-1-yl-amine (Example 32) (171.6 mg, 0.5 mmol), cyclopropylboronic acid (85.9 mg, 1.0 mmol), tricyclohexylphosphine (28 mg, 0.1 mmol), potassiumphosphate (371.5 mg, 1.75 mmol) and palladium actetate (11.2 mg, 0.05 mmol) in toluene (2 ml) and water (0.1 ml) was heated in a sealed tube at 110° C. for 17 h. The reaction mixture was poured into water (20 ml), extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with water (20 ml) and brine (20 ml), dried (magnesium sulfate) and evaporated. Further purification by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/heptane) yielded the title compound as colorless gum (69 mg, 41%). MS (ISP): m/e=305.2 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. washThe combined organic layers were washed with water (20 ml) and brine (20 ml)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. customFurther purification by flash chromatography (ethyl acetate/heptane)
  6. customon silica gel and crystallization (dichloromethane/heptane)

Sources & evidence

ORD record
ord-8e5b35da1cc4462698da3a08c0b7653f
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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