4-Azaindole → Pyrrolo[3,2-b]pyridin-1-ylamine

HRID 2382006노트

반응식

HRID 2382006 반응식
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].[NH2:16]Cl>CN(C=O)C.CCOCC>[N:1]1([NH2:16])[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

6

반응물 3

HCID 92264-AzaindoleHCID 25423MonochloramineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 19601545Pyrrolo[3,2-b]pyridin-1-ylamine수율 62%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A solution of pyrrolo[3,2-b]pyridine (1.64 mmol) and potassium tert-butoxide (3.29 mmol) in DMF (7.3 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl. in ether (16.3 mL) is added drop-wise at rt and the reaction mixture is stirred at rt for 3 h. The reaction mixture is quenched with 5% Na2S2O3 aqueous solution (10 mL), and extracted with ether. The combined organic layer is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc to afford pyrrolo[3,2-b]pyridin-1-ylamine (136 mg, 62%) as a solid. MS: 134 (M+H); 1H NMR (300 MHz, CDCl3): δ 4.89 (br, 2N—H), 6.61 (d, H), 7.16 (m, H), 7.38 (d, H), 7.76 (d, H), 8.47 (d, H).

후처리

  1. customThe reaction mixture is quenched with 5% Na2S2O3 aqueous solution (10 mL)
  2. extractionextracted with ether
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with EtOAc

출처 및 근거

ORD 기록
ord-f197521691ef40888ecc2293e6b42c0b
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258130B2

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