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 2063983노트

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HRID 2063983 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

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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-0d3bff59888c4cf8851d24404084b2d1
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288408B2

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