Hydrochloric Acid → HCID 86724248, compound

HRID 873706Notes

Reaction equation

HRID 873706 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:13]3([CH2:17][O:16][C:15]([N:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[N:14]3)[C:10]3([CH2:12][CH2:11]3)[CH2:9][O:8][C:5]2=[CH:6][CH:7]=1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C[Si]([N-:55][Si](C)(C)C)(C)C.[Li+].Cl>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].CO>[NH2:55][C:2]1[CH:3]=[C:4]2[C:13]3([CH2:17][O:16][C:15]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[N:14]3)[C:10]3([CH2:12][CH2:11]3)[CH2:9][O:8][C:5]2=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 86724230HCID 86724230, compound

Product 1

HCID 86724248HCID 86724248, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of di-tert-butyl (6′-bromodispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl)imidodicarbonate (200 mg, 0.393 mmol), bis(dibenzylideneacetone)palladium (0) (22.6 mg, 0.039 mmol), and tri-tert-butylphosphonium tetrafluoroborate (11.6 mg, 0.039 mmol) was added lithium bis(trimethylsilyl)amide (1 M in toluene, 1.96 mL, 1.96 mmol) at ambient temperature. After stirring for 1 hour at 100° C., the mixture was cooled down to ambient temperature. To the mixture were added 1M aqueous HCl (1.96 mL) and MeOH (1.96 mL) at ambient temperature, and the mixture was stirred for 30 minutes at the same temperature. The mixture was extracted with CHCl3, and the organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated at reduced pressure and purified with column chromatography on silica gel (hexane-EtOAc, a linear gradient of EtOAc from 0 to 90%) to afford tert-butyl (6′-aminodispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]oxazol]-2″-yl)carbamate (103 mg).

Workup

  1. temperaturethe mixture was cooled down to ambient temperature
  2. stirringthe mixture was stirred for 30 minutes at the same temperature
  3. extractionThe mixture was extracted with CHCl3
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated at reduced pressure
  7. custompurified with column chromatography on silica gel (hexane-EtOAc

Sources & evidence

ORD record
ord-4de3b76a78e9453faf1569d3c2da1641
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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