Sodium ethoxide → HCID 66743453, compound

HRID 1259351Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([C:17]#[C:18][Si](C)(C)C)[C:14]([C:23]([NH:25][C:26]3[CH:27]=[N:28][N:29]([CH2:31][C:32]([F:35])([F:34])[F:33])[CH:30]=3)=[O:24])=[CH:13][CH:12]=2)[CH:6]=[N:7][C:8]=1[O:9][CH3:10].CC[O-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]3[C:17](=[CH2:18])[N:25]([C:26]4[CH:27]=[N:28][N:29]([CH2:31][C:32]([F:35])([F:34])[F:33])[CH:30]=4)[C:23](=[O:24])[C:14]3=[CH:13][CH:12]=2)[CH:6]=[N:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 0 °C

Procedure

As shown in step 22-iv of Scheme 22, to a solution of 6-(5,6-dimethoxy-3-pyridyl)-N-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]-2-(2-trimethylsilylethynyl)pyridine-3-carboxamide (Compound 2070, 540 mg, 1.07 mmol) in EtOH (18.5 mL) at 23° C. was added dropwise EtONa (165 μL of a 1.3 M solution in EtOH, 0.214 mmol). After 25 min, the resulting slurry was cooled to 0° C. and, after stirring for 10 min at 0° C., the slurry was filtered, and the collected solid was washed with ice-cold EtOH (3×10 mL) to give 2-(5,6-dimethoxy-3-pyridyl)-7-methylene-6-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]pyrrolo[3,4-b]pyridin-5-one (Compound 2071, 436 mg, 93%) as a pale yellow solid after drying in vacuo: ESMS (M+H) 432.52; 1H NMR (CDCl3, 300 MHz) δ 8.38 (d, J=1.96, 1 H), 8.15 (d, J=8.13, 1 H), 7.88 (d, J=1.98, 1 H), 7.84 (s, 1H), 7.82 (d, J=8.16 Hz, 1H), 7.74 (s, 1H), 5.86 (d, J=1.89, 1 H), 5.11 (d, J=1.89, 1 H), 4.72 (q, J=8.32, 2 H), 4.05 (s, 3H), 3.96 (s, 3H).

Workup

filtrationthe slurry was filtered
washthe collected solid was washed with ice-cold EtOH (3×10 mL)

Sources & evidence

ORD record: ord-e544116cc7ff4dd2884a6f3f6c2db1d3
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466288B2

Reaction notes

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