HCID 53251717, compound → HCID 53251718, compound

HRID 1515775Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:17]2[NH:25][C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)=[CH:12]\[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>[Pd].CO>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:17]2[NH:25][C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2-[(E)-1-(4-methanesulfonyl-phenyl)-3,3-dimethyl-but-1-enyl]-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 73, 40 mg, 0.11 mmol) and 10% palladium on activated carbon (12 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 catalyst filtered off, washed with ethyl acetate and concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-[1-(4-methanesulfonyl-phenyl)-3,3-dimethyl-butyl]-1H-pyrrolo[2,3-b]pyridine (10 mg, 25%) as a white solid: LC/MS m/e calcd for C20H24N2O2S [M+H]+ 357.49, observed 357.4; 1H NMR (400 MHz, CD3OD) δ ppm 8.09 (br. s., 1H), 7.84-7.93 (m, 3H), 7.65 (d, J=8.3 Hz, 2H), 7.05 (dd, J=7.7, 4.9 Hz, 1H), 6.43 (s, 1H), 4.41-4.47 (m, 1H), 3.04-3.15 (m, 3H), 2.40 (dd, J=14.0, 7.7 Hz, 1H), 1.99-2.06 (m, 1H), 0.91 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-7f3ac8efce0a4806abac38036ec706fa
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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