Sodium Carbonate → 7-Iodo-1,5-naphthyridine 1-oxide

HRID 509639노트

반응식

HRID 509639 반응식
[I:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[CH:7][CH:6]=2.ClC1C=C(C=CC=1)C(OO)=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[I:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N+:9]2[O-:17])=[N:4][CH:3]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 497615953-Iodo-1,5-naphthyridine

생성물 1

HCID 679930227-Iodo-1,5-naphthyridine 1-oxide수율 54.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-iodo-1,5-naphthyridine (D-14) (2.750 g, 10.7 mmol, 1.0 eq) in CH2Cl2 (30 mL), 3-chloroperoxybenzoic acid (2.780 g, 16.1 mmol, 1.5 eq) was added. After the resulting mixture was stirred at RT for 2 h, saturated sodium carbonate solution (50 mL) was added, and extracted with CH2Cl2 (10×30 mL). The combined organic layers were dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (50% EA-PE) to afford the desired product 7-iodo-1,5-naphthyridine 1-oxide (D-15) (1.574 g, 54% yield) as a solid. 1H NMR (400 MHz, CDCl3-d6) δ: 9.45 (dd, J=2.0 Hz, J=0.8 Hz, 1H), 9.18 (d, J=2.5 Hz, 1H), 8.54 (d, J=6.0 Hz, 1H), 7.98 (d, J=8.8 Hz, 1H), 7.59-7.55 (m, 1H); ESI-MS m/z: 272.95 [M+H]+.

후처리

  1. extractionextracted with CH2Cl2 (10×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe resultant residue was purified by silica gel column chromatography (50% EA-PE)

출처 및 근거

ORD 기록
ord-44c8ea3f565c4cd789b20ee9e51731dd
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096590B2

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