Cesium carbonate → HCID 67383534, compound

HRID 335972Notes

Reaction equation

HRID 335972 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][CH2:12][B-](F)(F)F)([CH3:10])([CH3:9])[CH3:8].[K+].[Br:18][C:19]1[CH:20]=[C:21]2[C@@:33]3([CH2:37][O:36][C:35]([NH2:38])=[N:34]3)[C:32]3[C:27](=[N:28][CH:29]=[C:30](I)[CH:31]=3)[O:26][C:22]2=[CH:23][C:24]=1[F:25].O1CCOCC1>CCOC(C)=O.C([Pd-2](Cl)=C1N(C2C(CCC)=CC=CC=2CCC)CCN1C1C(CCC)=CC=CC=1CCC)C=C.O>[Br:18][C:19]1[CH:20]=[C:21]2[C@@:33]3([CH2:37][O:36][C:35]([NH2:38])=[N:34]3)[C:32]3[C:27](=[N:28][CH:29]=[C:30]([CH2:12][O:11][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:31]=3)[O:26][C:22]2=[CH:23][C:24]=1[F:25]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 45588181Potassium (tert-butoxymethyl)(trifluoro)borate(1-)HCID 58466189HCID 58466189, compound

Product 1

HCID 67383534HCID 67383534, compoundYield 19.91%

Reagents, catalysts & solvents 3

HCID 178455861HCID 178455861, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A vial charged with allylchloro[1,3-bis(2,6-di-1-propylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(ii) (0.072 g, 0.126 mmol), cesium carbonate (1.10 g, 3.36 mmol), potassium tert-butoxymethyltrifluoroborate (0.49 g, 2.52 mmol), and (S)-7-bromo-8-fluoro-3-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.40 g, 0.84 mmol, prepared as described in Method BB24) was treated with 3 mL dioxane and 0.3 mL water, was capped under argon, and was heated to 130° C. overnight. The reaction mixture was diluted with EtOAc, dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography gave (S)-7-bromo-3-(tert-butoxymethyl)-8-fluoro-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.073 g, 0.167 mmol, 19.91% yield) with impurities.

Workup

  1. customwas capped under argon
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification of the crude residue by column chromatography

Sources & evidence

ORD record
ord-0c16b0c42f0e41d4bb9a9ff84c1c259f
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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