Cesium carbonate → HCID 89761912, compound

HRID 528631Notes

Reaction equation

HRID 528631 reaction equation
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.[Cl:11][C:12]1[CH:13]=[CH:14][C:15](F)=[C:16]([CH:19]=1)[C:17]#[N:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:15]2[CH:14]=[CH:13][C:12]([Cl:11])=[CH:19][C:16]=2[C:17]#[N:18])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 936535-Chloro-2-fluorobenzonitrileHCID 5850963,4-Dihydro-2H-1,4-benzoxazine

Product 1

HCID 89761912HCID 89761912, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,4-dihydro-2H-benzo[b][1,4]oxazine (500 mg, 3.69 mmol, Tyger Scientific) and 5-chloro-2-fluorobenzonitrile (573 mg, 3.69 mmol) in DMF (10 mL) was added cesium carbonate (3.61 g, 11.0 mmol). The reaction mixture was heated at 100° C. for 24 h. After completion, the reaction mixture was quenched with ice water (10 mL) and extracted with ethyl acetate (2×15 mL). The organic layer was dried over sodium sulfate and concentrated to get crude material which was purified by column chromatography (12 g column: elution: 5% ethyl acetate in hexane) to provide 2-(2h-benzo[b][1,4]oxazin-4(3h)-yl)-5-chlorobenzonitrile (480 mg, 48.4%) as yellow solid. LCMS (ESI) m/z 270.02 (M+H).

Workup

  1. customAfter completion, the reaction mixture was quenched with ice water (10 mL)
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customto get crude material which
  6. customwas purified by column chromatography (12 g column: elution: 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7387588ce3c849f6ad37d9733274d25e
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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