Benzenesulfonyl chloride → HCID 68464675, compound

HRID 501187Notes

Reaction equation

HRID 501187 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][N:2]1[C:14]1[N:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][N:15]=1.CC(C)([O-])C.[K+].[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1.CCOC(C)=O.O.C1OCCOCCOCCOCCOCCOC1>[C:30]1([S:36]([N:12]2[C:13]3[CH2:1][N:2]([C:14]4[N:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][N:19]=4)[CH2:3][CH2:4][C:5]=3[C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

8

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 58703314HCID 58703314, compound

Product 1

HCID 68464675HCID 68464675, compoundYield 27.5%

Reagents, catalysts & solvents 4

HCID 2855718-Crown-6CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Example 8 (150 mg, 0.487 mmol) in THF (15 mL) was added potassium t-butoxide (81 mg, 0.720 mmol) and 18-crown-6 (2 mg) at 0° C. The suspension was stirred for 10-15 min at 0° C. and then benzenesulfonyl chlorde (0.86 mg, 0.486 mmol) was added. The reaction mixture was further stirred at 0° C. for 30 min. and then stirred at room temperature for 3 hours. The reaction mixture was diluted with EtOAc and water. The organic layer was washed with saturated sodium bicarbonate, dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography using EtOAc in hexanes (50%) to obtain methyl 2-[9-(phenylsulfonyl)-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidine-5-carboxylate (60 mg). 1HNMR (200 MHz, DMSO-d6) ppm: 8.8 (s, 2H), 8.14-7.25 (m, 9H), 5.42 (s, 2H), 4.26 (t, 2H, J=5.4 Hz), 3.91 (s, 3H), 2.81 (2H, t, J=5.4 Hz); m/e=449 (M+1).

Workup

  1. stirringThe reaction mixture was further stirred at 0° C. for 30 min.
  2. stirringstirred at room temperature for 3 hours
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-9f0ee5005ba64bdb97b44599243870f7
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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