Dimethylformamide → HCID 85997603, compound

HRID 2252238Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[C:7]1[NH:8][N:9]=[CH:10][C:6]=1[CH2:5]2.[Li]C1C=CC=CC=1.[Li]C(CC)C.CN([CH:31]=[O:32])C>C1COCC1>[CH3:15][O:14][C:13]1[CH:12]=[C:11]2[C:4]([CH2:5][C:6]3[CH:10]=[N:9][NH:8][C:7]=32)=[CH:3][C:2]=1[CH:31]=[O:32]

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of Example 104C (5.49 g, 0.0207 mol) in THF (300 mL) was added PhLi (1.9 M, 21.8 mL, 0.0414 mol) at −78° C. s-BuLi (1.4 M, 29.6 mL, 0.0414 mol) and DMF (12.8 mL, 0.166 mol) were added to the reaction mixture after 30 and 60 minutes, respectively. The mixture was stirred at −78° C. for 1 hour and the cold bath was removed. The reaction was quenched with saturated NH4Cl solution after 1 hour at room temperature. The mixture was extracted with EtOAc, washed with water, brine, dried over MgSO4, filtered, concentrated, and triturated with ether to give 3.62 g (81%) of the desired product. MS (DCI/NH3) m/z: 215.1 (M+H)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 3.62 (s, 2H) 4.01 (s, 3H) 7.45 (s, 1H), 7.73 (s, 1H) 7.80 (s, 1H) 10.37 (s, 1H) 13.07 (s, 1H).

Workup

additionwere added to the reaction mixture after 30 and 60 minutes
customthe cold bath was removed
customThe reaction was quenched with saturated NH4Cl solution after 1 hour at room temperature
extractionThe mixture was extracted with EtOAc
washwashed with water, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customtriturated with ether

Sources & evidence

ORD record: ord-fac2390ff7704c32ba1d519c2f63ad60
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320986B2

Reaction notes

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