Water → 1-(Phenylsulfonyl)-2-propyl-1H-pyrrolo[2,3-b]pyridine

HRID 893375Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH2:20][CH2:21][CH2:22]C.ICCC.O>O1CCCC1.CCCCCC>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH2:20][CH2:21][CH3:22])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 1-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine (400 mG, 1.55 mmol) in tetrahydrofuran (15 mL) at -78° C. was added n-BuLi (0.74 mL of a 2.5M solution in hexane, 1.86 mmol) dropwise. The mixture was stirred 1 h at -78° C. then warmed to rt for 5 min. The mixture was again cooled to -78° C. then iodo propane (0.45 mL, 4.65 mmol) was added and the mixture was stirred 1 h at rt. Water was added, and extractive workup (EtOAc) and purification (SiO2, 20% EtOAc/hexane) gave 1-(benzenesulfonyl)-2-propyl-1H-pyrrolo[2,3-b]-pyridine.

Workup

temperaturethen warmed to rt for 5 min
temperatureThe mixture was again cooled to -78° C.
stirringthe mixture was stirred 1 h at rt
customextractive workup (EtOAc) and purification (SiO2, 20% EtOAc/hexane)

Sources & evidence

ORD record: ord-0b35db46c9bd4803921b4761cd262e11
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05124335

Reaction notes

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