Potassium Iodide → HCID 89740938, compound

HRID 2206592Notes

Reaction equation

[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].[I-].[K+].Cl[CH:27]([CH3:31])[C:28](=[O:30])[CH3:29]>CC#N>[CH3:1][C:2]1[N:10]([CH:27]([C:28](=[O:30])[CH3:29])[CH3:31])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

Conditions

Temperature: 27 °C

Procedure

To a solution of tert-butyl 2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (5.0 g, 21.53 mmol) in CH3CN (50 mL) was added Cs2CO3 (21.0 g, 64.58 mmol), potassium iodide (3.57 g, 21.53 mmol). The mixture was stirred at 27° C. for 30 minutes. Then 3-chlorobutan-2-one (2.75 g, 25.83 mmol) was added and the mixture was stirred at 70° C. for 12 hours. The mixture was filtered and the filtrate was concentrated. The residue was purified by column (Elute: Petroleum ether:Ethyl acetate=50:1) to give tert-butyl 2-methyl-1-(3-oxobutan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate as a yellow-green oil. (3.23 g, yield 50%) LCMS (M+H+) m/z: calcd 303.37. found 302.9. 1H NMR (400 MHz, CDCl3): ä 8.32-8.30 (m, 1H), 8.25-8.23 (m, 1H), 7.17-7.14 (m, 1H), 5.50-5.44 (m, 1H), 2.71 (s, 3H), 1.96 (s, 3H), 1.65-1.67 (d, 3H), 1.64 (s, 9H).

Workup

stirringthe mixture was stirred at 70° C. for 12 hours
filtrationThe mixture was filtered
concentrationthe filtrate was concentrated
customThe residue was purified by column (Elute: Petroleum ether:Ethyl acetate=50:1)

Sources & evidence

ORD record: ord-82b4bf61a1ce46b5b01d1e0474fc2263
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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