Triphenylphosphine → HCID 67348768, compound

HRID 1029029Notes

Reaction equation

HRID 1029029 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]([NH2:26])=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][C:13](B2OC(C)(C)C(C)(C)O2)=[CH:12][CH:11]=3)[CH2:3][CH2:2]1.[Cl:27][C:28]1[C:29](I)=[C:30]([CH:35]=[CH:36][CH:37]=1)[C:31]([O:33][CH3:34])=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:26][C:8]1[C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:29]3[C:28]([Cl:27])=[CH:37][CH:36]=[CH:35][C:30]=3[C:31]([O:33][CH3:34])=[O:32])[CH:14]=2)[N:9]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 67325044HCID 67325044, compoundHCID 673479953-Morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

Product 1

HCID 67348768HCID 67348768, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
60 °C

Procedure

A vial was charged with 3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (1.07 g, 3 mmol, prepared as in Example 2, Step 1-2), methyl 3-chloro-2-iodobenzoate (889 mg, 3.00 mmol), Pd(OAc)2 (33.7 mg, 0.150 mmol), triphenylphosphine (79 mg, 0.300 mmol) and potassium phosphate (0.497 mL, 6.00 mmol). The vial was evacuated and backfilled with nitrogen gas 3×. Acetonitrile (8 mL) and Water (2 mL) were added and the reaction mixture was heated to 60° C. overnight in an oil bath. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was separated and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography (5% MeOH in DCM). Methyl 2-(2-amino-3-morpholinoquinolin-6-yl)-3-chlorobenzoate was obtained as a yellow powder.

Workup

  1. customThe vial was evacuated
  2. additionAcetonitrile (8 mL) and Water (2 mL) were added
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography (5% MeOH in DCM)

Sources & evidence

ORD record
ord-70aa5503dae54392bac71c38419d96f6
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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