Toluene → HCID 178504566, compound

HRID 61864Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][C:14]=1[Cl:15])[NH:11][C:10]1[C:9]([CH3:17])([CH3:16])[C:8]3[CH:18]=[C:19]([OH:22])[CH:20]=[CH:21][C:7]=3[C:6](=[O:23])[C:5]2=1.[Si:24]([O:31][CH2:32][C@H:33]1[O:37][C:36]([CH3:39])([CH3:38])[O:35][C@@H:34]1O)([C:27](C)(C)C)([CH3:26])C.[C:41]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:60]1([CH3:66])[CH:65]=CC=C[CH:61]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:60]([C@@H:32]([O:31][SiH:24]([CH3:26])[CH3:27])[C@@H:33]1[O:37][C:36]([CH3:38])([CH3:39])[O:35][CH:34]1[CH2:41][O:22][C:19]1[CH:20]=[CH:21][C:7]2[C:6](=[O:23])[C:5]3[C:4]4[C:12](=[CH:13][C:14]([Cl:15])=[C:2]([Cl:1])[CH:3]=4)[NH:11][C:10]=3[C:9]([CH3:17])([CH3:16])[C:8]=2[CH:18]=1)([CH3:66])([CH3:65])[CH3:61]

Participants

Conditions

Temperature: 40 °C

Procedure

Under nitrogen atmosphere, to the THF (0.3 mL) solution of 2,3-dichloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound Y4, 12.9 mg, 0.0373 mmol), (4S,5R)-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ol (15.5 mg, 0.0559 mmol) and triphenylphosphine (14.7 mg, 0.0559 mmol), toluene solution (25.4 μL, 0.0559 mmol) of DEAD was added dropwise at room temperature. The reaction mixture was stirred at ambient temperature of 40° C. for 4 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure, and the resulting crude product was purified by preparative TLC (Merck 60 F254, 0.5 mm) {solution for elution:hexane/ethyl acetate (3:1)} to obtain the title compound (white solid, 15.1 mg, 67%).

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated under reduced pressure
customthe resulting crude product was purified by preparative TLC (Merck 60 F254, 0.5 mm)
washfor elution

Sources & evidence

ORD record: ord-c076607dd855488094b4e339807f6902
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440922B2

Reaction notes

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