Реакция #90764

Уравнение реакции

2,5-dichloro-4-iodopyridine

2-aminobenzoic acid

DPEPhos

K3PO4

→

title compound

Выход 73.0%

2-[(2,5-Dichloro-4-pyridinyl)amino]benzoic acid

Выход 73.0%

Условия реакции

Обработка

1. 1
   Другоеwas degassed
2. 2
   workup.WAITleft
3. 3
   workup.ADDITIONAdded another 160 mg of Pd(OAc)2 to the mixture
4. 4
   Температураheated to 120° C. for another 24 h
5. 5
   ТемператураThe mixture was cooled to room temperature
6. 6
   Фильтрацияfollowed by filtration
7. 7
   Промывкаwashing with EtOAc
8. 8
   Фильтрацияfollowed by filtration
9. 9
   Другоеcollected solids could not
10. 10
    Другоеbe dried completely
11. 11
    ФильтрацияThe resulting paste was filtered
12. 12
    Промывкаwashed with water and TBME
13. 13
    СушкаThe solid was dried under vacuum over P2O5 for 2 days

Методика

A mixture of 2,5-dichloro-4-iodopyridine (10 g, 36.5 mmol), 2-aminobenzoic acid (4.85 g, 35.4 mmol), DPEPhos [bis(2-diphenylphosphinophenyl)ether] (1.6 g, 2.97 mmol), palladium(II) acetate (160 mg, 0.713 mmol) and K3PO4 (20 g, 94 mmol) was degassed and heated at 120° C. (oil bath temp) for 20 h. After 20 h, LCMS showed there was 33% (relative to the desired product) starting material left. Added another 160 mg of Pd(OAc)2 to the mixture, and heated to 120° C. for another 24 h. LCMS showed conversion complete. The mixture was cooled to room temperature, followed by filtration, and washing with EtOAc. The solids were acidified to pH=7-8, followed by filtration. However, the mixture was a paste, and collected solids could not be dried completely. The solids (11 g) was acidified with 6N HCl to pH=1. The resulting paste was filtered, and washed with water and TBME. The solid was dried under vacuum over P2O5 for 2 days to give the title compound (7.32 g, 60.2% yield). MS: M(C12H8Cl2N2O2)=283.11, (M+H)+=283.8; 1H NMR (400 MHz, DMSO) ppm 13.6 (s, 1 H) 10.2 (s, 1 H) 8.3 (s, 1 H) 8.0 (d, 1 H) 7.6 (q, 2 H) 7.3 (s, 1 H) 7.2 (m, 1 H).

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