Methanol → HCID 68853836, compound

HRID 1984052Notes

Reaction equation

Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].CO.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C[C:79](C)([O-:81])C.[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:79][O:81][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22]

Participants

Conditions

Temperature: 140 °C

Procedure

Into a 5 mL microwave flask 4-bromo-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2.4.AaBa, 0.3 g, 0.6 mmol) was dissolved in methanol (2 mL, 0.05 mol). Bis(dibenzylideneacetone)palladium(0) (0.02 g, 0.03 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.02 g, 0.03 mmol), and potassium tert-butoxide (0.5 mL, 4 mmol) were then added. The reaction was heated in the microwave oven at 140° C. for 1 h. The solvent was evaporated and prep-HPLC was performed to yield product 2K in 20% yield as a white, crystalline solid. MS analysis (m+1)=437.6.

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-360665328a114b338f9279071bb337bf
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544676B2

Reaction notes

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