Cesium carbonate → HCID 123573018, compound

HRID 2203685Notes

Reaction equation

HRID 2203685 reaction equation
[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25]2[NH:29][N:28]=[C:27]([C:30]3[CH:31]=[C:32]([O:37][C:38]([F:41])([F:40])[F:39])[C:33]([NH2:36])=[N:34][CH:35]=3)[CH:26]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:49][CH:50]1[CH2:52][CH2:51]1>CN(C)C=O>[Si:1]([O:18][CH:19]1[CH2:24][CH:23]2[CH:21]([CH:22]2[C:25]2[N:29]([CH2:49][CH:50]3[CH2:52][CH2:51]3)[N:28]=[C:27]([C:30]3[CH:31]=[C:32]([O:37][C:38]([F:41])([F:39])[F:40])[C:33]([NH2:36])=[N:34][CH:35]=3)[CH:26]=2)[CH2:20]1)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 123334776HCID 123334776, compound

Product 1

HCID 123573018HCID 123573018, compoundYield 135.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round-bottomed flask charged with 5-(5-(3-((tert-butyldiphenylsilyl)oxy)bicyclo[3.1.0]hexan-6-yl)-1H-pyrazol-3-yl)-3-(trifluoromethoxy)pyridin-2-amine (0.40 g, 0.35 mmol) and cesium carbonate (0.68 g, 2.1 mmol) in N,N-dimethylformamide (4 mL) was added bromomethylcyclopropane (0.28 mg, 2.1 mmol) at 20° C. After 16 h, the reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organics were washed with saturated aqueous sodium chloride solution (2×10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (30% ethyl acetate in petroleum ether) afforded product as an orange oil (0.30 g, 69% yield). LCMS (ESI) [MH]+=633.1.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate (20 mL) and water (10 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL)
  3. washThe combined organics were washed with saturated aqueous sodium chloride solution (2×10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-c6e45cbe165346369f4a98ba6c3238bf
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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