Oxalyl chloride → HCID 58980664, 화합물

HRID 735788노트

반응식

HRID 735788 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[N:16]([CH3:18])[C:15]([C:19]([OH:21])=O)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)C(C)C)(C)C.[C:37]([C:41]1[CH:46]=[C:45]([NH2:47])[C:44]([O:48][CH3:49])=[CH:43][N:42]=1)([CH3:40])([CH3:39])[CH3:38].C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C)C=O>[C:37]([C:41]1[CH:46]=[C:45]([NH:47][C:19]([C:15]2[N:16]([CH3:18])[C:17]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][C:9]=3[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:21])[C:44]([O:48][CH3:49])=[CH:43][N:42]=1)([CH3:40])([CH3:38])[CH3:39]

참가 물질

8

반응물 5

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 23540367HCID 23540367, 화합물HCID 58980614HCID 58980614, 화합물

생성물 1

HCID 58980664HCID 58980664, 화합물수율 100.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

To a slurry of 7-benzyloxy-1-methyl-1H-indole-2-carboxylic acid (163 mg, 0.58 mmol) in methylene chloride (2 mL) at 0° C. was added oxalyl chloride (72 microL, 0.84 mmol) followed by a drop of N,N-dimethylformamide. The solution immediately bubbled and became clear after a period of 0.75 h. The mixture was concentrated and redissolved in methylene chloride (1.5 mL). The acid chloride solution was added to a solution of N,N-diisopropylethylamine (202 microL, 1.16 mmol) and 2-tert-butyl-5-methoxy-pyridin-4-ylamine (95 mg, 0.52 mmol) in methylene chloride (1.5 mL). The solution was stirred at room temperature for 3 h then poured onto saturated aqueous NaHCO3. The aqueous layer was extracted with methylene chloride and the combined extracts were washed with saturated aqueous NaHCO3, followed by saturated aqueous KH2PO4, and again with saturated aqueous NaHCO3. The organic extracts were dried over sodium sulfate, filtered through a plug of silica-gel with diethyl ether, and concentrated in vacuo to provide pure 7-benzyloxy-1-methyl-1H-indole-2-carboxylic acid (2-tert-butyl-5-methoxy-pyridin-4-yl)-amide (231 mg, 99%) as a white solid.

후처리

  1. customThe solution immediately bubbled
  2. concentrationThe mixture was concentrated
  3. dissolutionredissolved in methylene chloride (1.5 mL)
  4. extractionThe aqueous layer was extracted with methylene chloride
  5. washthe combined extracts were washed with saturated aqueous NaHCO3
  6. dry with materialThe organic extracts were dried over sodium sulfate
  7. filtrationfiltered through a plug of silica-gel with diethyl ether
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b1d6e55b064d4f598e89a7f740c3ad5f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592332B2

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