P-Anisidine → HCID 87126354, compound

HRID 929613Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1.CC1C=CC(S(O[CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][C:34]#[CH:35])(=O)=O)=CC=1>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][C:34]#[CH:35])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

K2CO3 (380 mg, 2.76 mmol, 2.5 equiv.) was added to a solution of 4-methoxyaniline (136 mg, 1.1 mmol, 1 equiv.) in 1 mL of DMF, and the resulting slurry was heated to 100° C. 2-(2-(prop-2-ynyloxy)ethoxy)ethyl 4-methylbenzenesulfonate (s-8) (100 mg, 0.276 mmol, 0.25 equiv.), dissolved in DMF (1 mL), was then added to the reaction via syringe-pump over 5 hours. The reaction was stirred for an additional 12 hours, after which time it was concentrated under reduced pressure and partially purified (Silica Gel, 12 g RediSep pre-packed column, 0% EtOAc:Hexanes→20% EtOAc:Hexanes→50% EtOAc:Hexanes, followed by EtOAc flush). The material obtained after chromatography was carried directly on to the next step without further purification.

Workup

additionwas then added to the reaction via syringe-pump over 5 hours
concentrationafter which time it was concentrated under reduced pressure
custompartially purified
custom(Silica Gel, 12 g RediSep pre-packed column, 0% EtOAc:Hexanes→20% EtOAc:Hexanes→50% EtOAc:Hexanes, followed by EtOAc flush)
customThe material obtained after chromatography
customwas carried directly on to the next step without further purification

Sources & evidence

ORD record: ord-a63ba83477934dce887c5b845951cbb5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296708B2

Reaction notes

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