2-(4-Bromo-2-fluorophenylamino)-6-formylaminomethylnicotinic acid methyl ester → 5-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester

HRID 2076164노트

반응식

HRID 2076164 반응식
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH:12]=O)=[N:6][C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22].O(Cl)Cl.[P+5]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:6]([CH:12]=[N:11][CH:10]=2)[C:5]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[F:22])=[O:23]

참가 물질

4

반응물 2

HCID 591401622-(4-Bromo-2-fluorophenylamino)-6-formylaminomethylnicotinic acid methyl esterHCID 178479711HCID 178479711, 화합물

생성물 1

HCID 591401535-(4-Bromo-2-fluorophenylamino)-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester수율 49%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
95 °C

실험 절차

To a solution of 2-(4-Bromo-2-fluorophenylamino)-6-formylaminomethylnicotinic acid methyl ester (11.8 g, 30.9 mmol) in toluene (550 mL) was added phosphorous (V) oxychloride (3.16 mL, 34 mmol) and the reaction mixture heated at 95° C. for 1 hour. The reaction mixture was concentrated in vacuo and treated with aqueous saturated sodium hydrogen carbonate solution then extracted twice with ethyl acetate. The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si-PPC, gradient 0-30% ethyl acetate in DCM) to yield the title compound as a brown oil (5.4 g, 49%). LCMS (Method B): RT=3.56 min, M+H+=364/366.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiontreated with aqueous saturated sodium hydrogen carbonate solution
  3. extractionthen extracted twice with ethyl acetate
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0054c2e06f194b4ca59f4d7e1911cb2f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923456B2

반응 노트

불러오는 중…