2-{1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-3-methyl-but-1-enyl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine → 1H-Pyrrolo(2,3-b)pyridine

HRID 1515837Notes

Reaction equation

C(OCCS(C1C=CC(C([C:20]2[NH:29][C:23]3=[N:24][CH:25]=[C:26](F)[CH:27]=[C:22]3[CH:21]=2)=CC(C)C)=CC=1)(=O)=O)C>[Pd].CO>[NH:29]1[C:23]2=[N:24][CH:25]=[CH:26][CH:27]=[C:22]2[CH:21]=[CH:20]1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-{1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-3-methyl-but-1-enyl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine (160 mg, 0.38 mmol) and 10% palladium on activated carbon (70 mg) in methanol (250 mL) was heated at 50° C. under hydrogen (50 psi) for 16 h. The mixture was cooled to 25° C., the solids filtered off, washed with ethyl acetate and concentrated in vacuo to afford 2-{1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-3-methyl-butyl}-5-fluoro}-1H-pyrrolo[2,3-b]pyridine (150 mg, 93%) which was used in the next step without further purification: LC/MS m/e calcd for C22H27FN2O3S [M+H]+ 419.53, observed 419.0.

Workup

temperatureThe mixture was cooled to 25° C.
filtrationthe solids filtered off
washwashed with ethyl acetate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-176b0a34ce6c41edba766cd5f0159cb8
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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