Methanesulfonyl chloride → HCID 67436917, compound

HRID 1663406Notes

Reaction equation

HRID 1663406 reaction equation
CS(Cl)(=O)=O.[CH3:6][N:7]([CH3:37])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]3[O:22][C:23]4[C:28]([CH:29]([CH:30]([CH2:35]O)[C:31]([O:33][CH3:34])=[O:32])[C:19]3=[CH:18][CH:17]=2)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:12][CH:11]=1)=[O:9].C1CCN2C(=NCCC2)CC1.C([O-])(O)=O.[Na+]>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(OCC)(=O)C>[CH3:37][N:7]([CH3:6])[C:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[N:21]=[C:20]3[O:22][C:23]4[C:28]([CH:29]([C:30](=[CH2:35])[C:31]([O:33][CH3:34])=[O:32])[C:19]3=[CH:18][CH:17]=2)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:14][CH:15]=1)=[O:9]

Participants

8

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516892Sodium BicarbonateHCID 67436091HCID 67436091, compound

Product 1

HCID 67436917HCID 67436917, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.072 mL, 0.925 mmol) was added to a mixture of the product from Step 2 (80 mg, 0.185 mmol), TEA (0.258 mL, 1.85 mmol) and DMAP (24.9 mg, 0.203 mmol) in DCM (2 mL) at 0° C. After 1 h at this temperature, the mixture was concentrated in vacuo. The residue was suspended in benzene (4 mL), treated with DBU (0.139 mL, 0.925 mmol) and stirred at room temperature for 1 h. Saturated NaHCO3 (5 mL) and ethyl acetate (100 mL) were added. The mixture was washed with water (2×10 mL), brine (10 mL), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica, 50-100% ethyl acetate in hexanes) to provide methyl 2-(2-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)acrylate (45 mg, 59%). MS (ES+) m/z: 415 (M+H); HPLC retention time: 1.73 min (Analytical HPLC Method F).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. washThe mixture was washed with water (2×10 mL), brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (silica, 50-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2720ad7f78754da5ba40afa5149855a7
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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