Cesium carbonate → HCID 67383100, compound

HRID 335967Notes

Reaction equation

Br[C:2]1[CH:15]=[C:14]([F:16])[C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:17][CH3:18])=[CH:9][CH:10]=3)[C@@:5]3([CH2:22][O:21][C:20]([NH2:23])=[N:19]3)[C:4]=2[CH:3]=1.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:72]1[CH2:76][CH2:75][CH2:74][C:73]1=[O:77]>CCOC(C)=O.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[NH2:23][C:20]1[O:21][CH2:22][C@:5]2([N:19]=1)[C:6]1[CH:7]=[C:8]([O:17][CH3:18])[CH:9]=[CH:10][C:11]=1[O:12][C:13]1[C:4]2=[CH:3][C:2]([N:72]2[CH2:76][CH2:75][CH2:74][C:73]2=[O:77])=[CH:15][C:14]=1[F:16]

Participants

Conditions

Temperature: 100 °C

Procedure

Resealable tube was charged with solids: (S)-2′-bromo-4′-fluoro-7′-methoxy-5H-spiro[oxazole-4,9′-xanthen]-2-amine (500 mg, 1.32 mmol, prepared as described in Method BB40 but using 4-bromo-2-fluorophenol and 2-bromo-5-methoxybenzoic acid)), Pd2 dba3 (121 mg, 0.13 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (229 mg, 0.40 mmol), cesium carbonate (859 mg, 2.64 mmol). pyrrolidin-2-one (152 μL, 1.98 mmol) and dioxane (5 ml) were added and the mixture was stirred at 100° C. for 60 h. The mixture was diluted with EtOAc, filtered through celite, concentrated and purified on 12 g RediSep Gold column using 10-80% of DCM/MeOH/NH4OH 90:10:1 in DCM to afford (S)-1-(2-amino-5′-fluoro-2′-methoxy-5H-spiro[oxazole-4,9′-xanthene]-7′-yl)pyrrolidin-2-one.

Workup

additionResealable tube was charged with solids
filtrationfiltered through celite,
concentrationconcentrated
custompurified on 12 g RediSep Gold column

Sources & evidence

ORD record: ord-91427fe1ce03479182598cdf2998cdba
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

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