Potassium Phosphate, Tribasic → HCID 44217197, compound

HRID 1671572Notes

Reaction equation

HRID 1671572 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3I)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]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.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:22]1([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18]=2[CH:19]=[CH:20][C:11]([NH:10][C@H:1]2[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:3][CH2:2]2)=[N:12]3)[CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 67095932HCID 67095932, compound

Product 1

HCID 44217197HCID 44217197, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

(R)-Indan-1-yl-(5-iodo-quinolin-2-yl)-amine (example 1, step A, 2000 mg, 0.52 mmol) was dissolved in 5 mL toluene and 0.15 mL water. Cyclopropylboronic acid (89 mg, 1.04 mmol) was added. Argon was bubbled through the solution for 2 minutes to remove oxygen. Tri(cyclohexyl)-phosphine (30 mg, 0.11 mmol), palladium acetate (12 mg, 0.05 mmol) and tri-potassium phosphate (385 mg, 1.8 mmol) were added. The reaction mixture was evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→75:25 gradient). The title compound was obtained as a white gum (114 mg, 73%), MS: m/e=301.3 (M+H+).

Workup

  1. customArgon was bubbled through the solution for 2 minutes
  2. customto remove oxygen
  3. customThe reaction mixture was evaporated
  4. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→75:25 gradient)

Sources & evidence

ORD record
ord-fa5ba13405d74c4eb93f0d9c85c77125
Source dataset
uspto-grants-2011_08
Patent number
US07994324B2

Reaction notes

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