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

HRID 966115노트

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HRID 966115 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21226129Dichloromethane methanol용매2회

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온도
65 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-d4b66ce51b9c4364b3bcc0e61489b067
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951851B2

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