HCID 67228219, compound → HCID 58305228, compound

HRID 1515769Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](/[C:11](/[C:18]2[NH:26][C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=2)=[CH:12]/[CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>[Pd].CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:18]2[NH:26][C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH:19]=2)[CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (Z)-2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-furan-2-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (prepared as in Example 70, 60 mg, 0.16 mmol) and 10% palladium on activated carbon (18 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)-2-(tetrahydro-furan-2-yl)-ethyl]-1H-pyrrolo[2,3-b]pyridine (15 mg, 24%) as a mixture of stereoisomers: LC/MS m/e calcd for C20H22N2O3S [M+H]+ 371.47, observed 371.3; 1H NMR (400 MHz, CD3OD) δ ppm 8.12 (d, J=3.8 Hz, 1H), 7.90-8.00 (m, 3H), 7.62-7.67 (m, 2H), 7.06-7.11 (m, 1H), 6.43-6.48 (m, 1H), 4.50-4.61 (m, 2H), 3.83-3.97 (m, 1H), 3.65-3.78 (m, 2H), 3.11-3.19 (m, 3H), 2.43-2.55 (m, 1H), 2.21-2.36 (m, 1H), 1.85-2.11 (m, 3H), 1.57-1.67 (m, 1H).

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-4492885db6b04efaa3aa9628603c7e31
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222416B2

Reaction notes

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