Dimethylformamide → HCID 57549752, compound

HRID 1799347Notes

Reaction equation

C([Li])CCC.Br[C:7]1[N:8]=[C:9]([O:21][CH2:22][CH3:23])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[Cl:12].CN(C)CCN(C)C.CN([CH:35]=[O:36])C.[NH4+].[OH-]>C1COCC1>[Cl:12][C:11]1[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:9]([O:21][CH2:22][CH3:23])=[N:8][C:7]=1[CH:35]=[O:36]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (2.5M in hexanes, 1.2 mL) was added to a solution of intermediate (26a) (1.0 g, 2.8 mmol) and N,N,N′,N′-tetramethylethylenediamine (0.5 mL, 3.1 mmol) in THF (8 mL) at −78° C. DMF (0.3 mL, 3.4 mmol) was added after 3 minutes. The mixture was stirred at −78° C. for 1 hour. The mixture was allowed to warm to room temperature over 30 minutes. Saturated aq. NH4OH (1 mL) was added and the mixture was concentrated in vacuo. The mixture was extracted with DCM (2×30 mL) and 0.5M PO3H4 (10 mL). The combined organic fractions were washed with sat. aq. NaHCO3 (20 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Silica gel chromatography (EtOAc:hexane) afforded intermediate (26b) (600 mg).

Workup

temperatureto warm to room temperature over 30 minutes
concentrationthe mixture was concentrated in vacuo
extractionThe mixture was extracted with DCM (2×30 mL) and 0.5M
washThe combined organic fractions were washed with sat. aq. NaHCO3 (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-9bcf5db59ce34650b6c8d610be22fce7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344013B2

Reaction notes

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