Pyridine → Methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoate

HRID 335310

반응식

HRID 335310 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11](NC3C=C(C=CC=3F)C(O)=O)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.S(Cl)(Cl)=O.[NH2:28][C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][C:38]=1[CH3:39])[C:32]([O:34][CH3:35])=[O:33].N1C=CC=CC=1>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:28][C:29]3[CH:30]=[C:31]([CH:36]=[CH:37][C:38]=3[CH3:39])[C:32]([O:34][CH3:35])=[O:33])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 337778Methyl 3-amino-4-methylbenzoateHCID 712834433-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluorobenzoic acid2회

생성물 1

HCID 71283103Methyl 3-(7-bromoimidazo[1,2-a]pyridine-3-carboxamido)-4-methylbenzoate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture comprising 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate 1A step 3) (750 mg, 3.11 mmol) and thionyl chloride (5 ml, 68.5 mmol) under N2 was heated at reflux for 2 hrs. The mixture was concentrated in vacuo and azeotroped with toluene. Methyl 3-amino-4-methylbenzoate (514 mg, 3.11 mmol) (pre-dried at 45° C.) was added followed by pyridine (5 ml) and the mixture was stirred at room temperature under N2 overnight. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3, brine, H2O, dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with 50-100% EtOAc in iso-hexane afforded the title compound as an orange solid;

후처리

  1. temperatureat reflux for 2 hrs
  2. concentrationThe mixture was concentrated in vacuo
  3. customazeotroped with toluene
  4. washwashed with sat. NaHCO3, brine, H2O
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica eluting with 50-100% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-973abd30f88f43e5a53172b267f448f1
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883819B2

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