Potassium Phosphate, Tribasic → HCID 178419890, compound

HRID 1666113Notes

Reaction equation

HRID 1666113 reaction equation
Br[C:2]1[C:11]2[CH2:10][O:9][C:8]([NH:12][C@H:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][CH2:14]3)=[N:7][C:6]=2[CH:5]=[CH:4][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[C:11]3[CH2:10][O:9][C:8]([NH:12][C@H:13]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[CH2:15][CH2:14]4)=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 178419341HCID 178419341, compound

Product 1

HCID 178419890HCID 178419890, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

A stirred mixture of (5-bromo-4H-benzo[d][1,3]oxazin-2-yl) -(R)-indan-1-yl-amine (Example 10) (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 (MgSO4) and evaporated. Further purification by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/heptane) yielded the title compound as colorless gum (83 mg, 49%). 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 (MgSO4)
  4. customevaporated
  5. customFurther purification by flash chromatography (ethyl acetate/heptane)
  6. customon silica gel and crystallization (dichloromethane/heptane)

Sources & evidence

ORD record
ord-8069054cdea545dbaaa82fdd8f8fd0b5
Source dataset
uspto-grants-2011_10
Patent number
US08044047B2

Reaction notes

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