HCID 67155027, compound → HCID 69937586, compound

HRID 1897581Notes

Reaction equation

[C:1]([C:4]1[C:9]([F:10])=[CH:8][N:7]=[CH:6][C:5]=1[C:11]1[O:12][C:13]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:14]=2[CH:15]=1)(=[O:3])[CH3:2].[CH3:22][Mg]Br>C1COCC1>[F:10][C:9]1[C:4]([C:1]([OH:3])([CH3:22])[CH3:2])=[C:5]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][C:14]=3[CH:15]=2)[CH:6]=[N:7][CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To 2-(4-acetyl-5-fluoropyridin-3-yl)benzofuran-5-carbonitrile 11b (200 mg, 0.714 mmol) in THF (3.57 mL) at −78° C. was added methylmagnesium bromide (3M in Et2O, 0.714 mL, 2.142 mmol). The mixture was stirred for 1 hr at −78° C., and then for 1 hr at 0° C. The mixture was quenched with saturated NH4Cl and extracted with EtOAc two times, dried over magnesium sulfate, filtered and concentrated. The residue was purified via Biotage (10-40% EtOAc/heptane; SNAP25 column), and then purified on Waters mass directed preparative-HPLC (ACN—H2O—NR4OH, Xbridge Preparation C18 column, 30×100 mm) giving the title compound 11 (60 mg, 28%). 1H NMR (400 MHz, MeOD) δ ppm 1.70 (d, J=1.96 Hz, 6H) 6.94 (s, 1H) 7.55-7.71 (m, 2H) 8.00-8.11 (m, 1H) 8.39 (s, 1H) 8.53 (d, J=3.73 Hz, 1H). LC-MS (M+1) 297.1, t=1.50 min.

Workup

waitfor 1 hr at 0° C
customThe mixture was quenched with saturated NH4Cl
extractionextracted with EtOAc two times
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified via Biotage (10-40% EtOAc/heptane; SNAP25 column)
custompurified on Waters mass
custom(ACN—H2O—NR4OH, Xbridge Preparation C18 column, 30×100 mm)

Sources & evidence

ORD record: ord-467c8ddb914c4b05b189b10615025867
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519134B2

Reaction notes

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