Potassium Phosphate, Tribasic → Methyl 2-amino-5-cyclopropylbenzoate

HRID 41998

Reaction equation

HRID 41998 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].P(C1CCCCC1)(C1CCCCC1)C1CCCCC1>C1(C)C=CC=CC=1.O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH:13]2[CH2:15][CH2:14]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 736224Methyl 2-amino-5-bromobenzoateHCID 2760897Cyclopropylboronic acid

Product 1

HCID 13052309Methyl 2-amino-5-cyclopropylbenzoateYield 88.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

In a schlenck tube, a mixture of methyl 2-amino-5-bromobenzoate (43.47 mmol, 10 g), cyclopropylboronic acid (112.92 mmol, 9.700 g), K3PO4 (144.16 mmol, 30.6 g), Pd(AcO)2 (3.47 mmol, 0.780 g), P(Cy)3 (7.85 mmol, 2.2 g) in toluene (170 ml) and water (10 ml) was heated for 2 hours at 100° C., under nitrogen atmosphere. The reaction mixture was filtered through celite and the organic phase was separated and evaporated affording 7.34 g (yield 77%) of the expected product.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe organic phase was separated
  3. customevaporated

Sources & evidence

ORD record
ord-551834844ec144a489dbc19d16676188
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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