Methylamine → 4-Methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 733070노트

반응식

HRID 733070 반응식
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.ClC1C(C=O)=C[N:17]=[C:16]2N([Si](C(C)C)(C(C)C)C(C)C)C=CC=12.CN>COC(O)C>[CH3:16][NH:17][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12

참가 물질

5

반응물 3

HCID 6329MethylamineHCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehydeHCID 497590451H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 4-chloro-1-[tris(1-methylethyl)silyl]-

생성물 1

HCID 578391454-Methylamino-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

시약·촉매·용매 1

HCID 30156371-Methoxyethanol용매

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온도
110 °C

실험 절차

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde and 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (2.0 g, from above step), methylamine (40% solution in water, 16 mL, 100 mmol) in methoxy-ethanol (4 mL) is heated at 110° C. in a sealed tube overnight. The reaction mixture is cooled to room temperature and concentrated. The residue is dissolved in HCl solution (1N, 20 mL) and heated at 50° C. After stirring for 1.5 hours at 50° C., the reaction mixture is neutralized with saturated sodium bicarbonate solution to a pH of 8. The solid is collected by filtration and washed with water, then hexanes, dried to afford the title compound as a light yellow solid: MS m/z 176.1 (M+1).

후처리

  1. temperatureThe reaction mixture is cooled to room temperature
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in HCl solution (1N, 20 mL)
  4. temperatureheated at 50° C
  5. filtrationThe solid is collected by filtration
  6. washwashed with water
  7. dry with materialhexanes, dried

출처 및 근거

ORD 기록
ord-907f745ce57b4765843423eebb548528
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589101B2

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