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

HRID 273243ノート

反応式

HRID 273243 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c3faa1c2c0c543ebba0d3033dcf48bee
出典データセット
uspto-grants-2008_11
特許番号
US07456196B2

反応ノート

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