Benzenesulfonyl chloride → HCID 57856232, compound

HRID 500739Notes

Reaction equation

HRID 500739 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[C:10]([C:20]3[CH:21]=[C:22]4[CH:28]=[CH:27][NH:26][C:23]4=[N:24][CH:25]=3)=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[CH:13]=2)[CH:6]=[CH:5][N:4]=1.[H-].[Na+].[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[C:31]1([S:37]([N:26]2[C:23]3=[N:24][CH:25]=[C:20]([C:10]4[C:9]([C:7]5[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=5)=[CH:13][N:12]([CH:14]5[CH2:19][CH2:18][CH2:17][CH2:16][O:15]5)[N:11]=4)[CH:21]=[C:22]3[CH:28]=[CH:27]2)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 578562535-[4-(2-Methylsulfanyl-pyrimidin-4-yl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57856232HCID 57856232, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the 5-[4-(2-Methylsulfanyl-pyrimidin-4-yl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (C-1-1) (870 mg, 2.22 mmol) in DMF (10 mL) at 25° C. was added Sodium Hydride (60% dispersion in oil, 133 mg, 3.32 mmol). The resulting suspension was stirred at ambient temperature for a few minutes until gas evolution ceased. Benzenesulfonyl chloride (0.4 mL, 3.13 mmol) was added and the mixture became cloudy. After stirring at ambient temperature for 15 minutes, LCMS showed complete conversion to desired product. The mixture was added slowly to 150 ml of saturated aqueous NaCl. The resulting precipitate was filtered, washed with water, and air dried. The solids were dissolved in dichloromethane, dried over MgSO4 and reduced to minimum volume. The residue was purified on a short column of silica gel using a gradient of 0-20% ethyl acetate in dichloromethane as eluent to give 1-Benzenesulfonyl-5-[4-(2-methylsulfanyl-pyrimidin-4-yl)-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (C-1-2) (0.83 g, 70%) as a yellow foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.77 (s, 1H), 8.47 (d, J=5.31 Hz, 1H), 8.43 (d, J=2.02 Hz, 1H), 8.16 (d, J=2.02 Hz, 1H), 8.09-8.15 (m, 2H), 7.95 (d, J=4.04 Hz, 1H), 7.68-7.77 (m, 1H), 7.57-7.67 (m, 2H), 7.29 (d, J=5.05 Hz, 1H), 6.86 (d, J=4.04 Hz, 1H), 5.52 (dd, J=9.85, 2.27 Hz, 1H), 3.98 (br. d, J=11.87 Hz, 1H), 3.62-3.74 (m, 1H), 2.07-2.23 (br. m, 1H), 1.90-2.05 (br. m, 2H), 1.66-1.77 (br. m, 1H), 1.65 (s, 3H), 1.50-1.61 (br. m, 2H).

Workup

  1. stirringAfter stirring at ambient temperature for 15 minutes

Sources & evidence

ORD record
ord-d5d6b40983154950afc9564574e373a8
Source dataset
uspto-grants-2010_08
Patent number
US07772246B2

Reaction notes

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