Hydrochloric Acid → 6-bromo-1H-pyrrolo[3,2-b]pyridine 5-carbonitrile

HRID 75271ノート

反応式

HRID 75271 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[N:12](S(C3C=CC(C)=CC=3)(=O)=O)[CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[C:8]#[N:9].C1COCC1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:3]=[C:4]2[NH:12][CH:11]=[CH:10][C:5]2=[N:6][C:7]=1[C:8]#[N:9]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 867079606-Bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine 5-carbonitrile

生成物 1

HCID 867079616-bromo-1H-pyrrolo[3,2-b]pyridine 5-carbonitrile

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred mixture of 6-bromo-1-tosyl-1H-pyrrolo[3,2-b]pyridine 5-carbonitrile (2.46 g, 6.54 mmol), THF (6 mL) and MeOH (6 mL) was added 1N NaOH (3 mL). The reaction mixture was stirred for 30 minutes and then neutralized with 1N HCl and extracted with EtOAc (2×). The organic phase was dried over MgSO4 and concentrated in vacuo to give crude intermediate 6-bromo-1H-pyrrolo[3,2-b]pyridine 5-carbonitrile, which was subsequently dissolved in DMF (10 mL) and cooled to 0° C. Sodium hydride (60%, 314 mg, 7.85 mmol) was added, and the reaction mixture was stirred 30 minutes. Next, iodomethane (0.49 mL, 7.85 mmol) was added, and the reaction mixture was stirred for 30 minutes while warming to RT. The solution was subsequently diluted with EtOAc (100 mL), quenched and washed with brine. The aqueous layer was back-extracted with EtOAc (2×). The combined organic layers were dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (2% MeOH/DCM) to give the title compound as a white solid (1.05 g, 68%). 1H NMR (500 MHz, CDCl3) δ ppm 7.90 (s, 1H), 7.43 (d, 1H, J=3.5 Hz), 6.76 (d, 1H, J=3.5 Hz), 3.85 (s, 3H); ESI-MS m/z [M+H]+ calc'd for C9H6BrN3, 236, 238; found 236, 238.

後処理

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-293f95c71db7489198ad9c16b24cdb2a
出典データセット
uspto-grants-2014_09
特許番号
US08835420B2

反応ノート

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