Acetic Acid → 3-Bromo-7-(2-pyrrolidin-1-yl-ethyl)[1,5]naphthyridine

HRID 273243노트

반응식

HRID 273243 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH2:12][CH:13]=O)[CH:8]=[N:9]2)=[N:4][CH:3]=1.C(O)(=O)C.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C1COCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[N:9][CH:8]=[C:7]([CH2:12][CH2:13][N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH:6]=2

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 21043926(7-Bromo-1,5-naphthyridin-3-yl)acetaldehyde

생성물 1

HCID 104028693-Bromo-7-(2-pyrrolidin-1-yl-ethyl)[1,5]naphthyridine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of the product from Example 153D (0.1 g, 0.4 mmol), acetic acid (0.4 mmol, 0.025 g) and pyrrolidine (0.44 mmol, 0.031 g) in dry THF (5 ml) NaBH(OAc)3 was added (0.6 mmol, 0.127 g). After 12 hr at room temperature the mixture was diluted with 50 mL of CH2Cl2 and washed successively with a saturated solution of sodium bicarbonate, brine and water. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified over silica using 10% MeOH in CH2Cl2. The desired compound was obtained in 40%. 1H NMR (CDCl3, 300 MHz) δ 1.60 (m, 4H), 2.20 (m, 4H), 2.75 (m, 4H), 8.30 (m, 1H), 8.40 (m, 1H), 8.90 (m, 1H), 9.05 (m, 1H). MS (ESI) [M+H]+ at 307.

후처리

  1. washwashed successively with a saturated solution of sodium bicarbonate, brine and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified over silica using 10% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-c3faa1c2c0c543ebba0d3033dcf48bee
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456196B2

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