Morpholine → 5-morpholin-4-yl-1H-pyrrolo[2,3-c]pyridine

HRID 497364ノート

反応式

HRID 497364 の反応式
Cl[C:2]1[CH:7]=[C:6]([CH:8]=[CH:9][N:10](C)C)[C:5]([N+]([O-])=O)=[CH:4][N:3]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C([O-])=O.[NH4+]>[Pd].CO.C(Cl)Cl>[N:16]1([C:4]2[CH:5]=[C:6]3[CH:8]=[CH:9][NH:10][C:7]3=[CH:2][N:3]=2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

参加物

6

反応物 3

HCID 8083MorpholineHCID 2723923Ammonium formateHCID 4611300[2-(2-Chloro-5-nitro-pyridin-4-yl)-vinyl]dimethyl-amine

生成物 1

HCID 223120045-morpholin-4-yl-1H-pyrrolo[2,3-c]pyridine収率 52%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21226129Dichloromethane methanol溶媒2 回

反応条件

温度
65 °C

実験手順

A solution of 450 mg (2 mmol) of [2-(2-chloro-5-nitro-pyridin-4-yl)-vinyl]-dimethyl-amine in a 20 mL of mixed solvent of MeOH—CH2Cl2 (1:1) was treated with 3 mL of morpholine. The reaction mixture was stirred at 65° C. for 8 h. Volatiles were then removed. CH2Cl2 (100 mL) and H2O (30 mL) were added. The organic layer was separated and washed with H2O (30 mL), brine (30 mL), dried over Na2SO4, and concentrated. The red powder was treated with 4.0 g (63 mmol, 32 eq) of ammonium formate and 10% Pd—C (120 mg). The reaction mixture was stirred at 65° C. for 30 min. The reaction mixture was then filtered through a pad of celite and concentrated to obtain a yellow solid. Column chromatography (silica, 5% MeOH/CH2Cl2) provided 210 mg (52% for 2 steps) of 5-morpholin-4-yl-1H-pyrrolo[2,3-c]pyridine as a yellow solid. TLC (silica, 5% MeOH/CH2Cl2): Rf=0.40. MS (electrospray): exact mass calculated for C11H13N3O, 203.11; m/z found, 204.2 [M+H]+.

後処理

  1. customVolatiles were then removed
  2. additionCH2Cl2 (100 mL) and H2O (30 mL) were added
  3. customThe organic layer was separated
  4. washwashed with H2O (30 mL), brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. stirringThe reaction mixture was stirred at 65° C. for 30 min
  8. filtrationThe reaction mixture was then filtered through a pad of celite
  9. concentrationconcentrated
  10. customto obtain a yellow solid

出典と根拠

ORDレコード
ord-c3c7aaedff034cb69dd039a463f298be
出典データセット
uspto-grants-2005_09
特許番号
US06949540B2

反応ノート

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