Benzenesulfonyl chloride → N-[3-(7-Benzenesulfonyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide

HRID 589520Notes

Reaction equation

[C:1]([C:5]1[CH:29]=[CH:28][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:19]4[CH:26]=[CH:25][NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[C:13]=2[CH3:27])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[C:32]1([S:38](Cl)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[C:32]1([S:38]([N:24]2[C:20]3[N:21]=[CH:22][N:23]=[C:18]([C:14]4[C:13]([CH3:27])=[C:12]([NH:11][C:9](=[O:10])[C:8]5[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:29][CH:28]=5)[CH:17]=[CH:16][CH:15]=4)[C:19]=3[CH:26]=[CH:25]2)(=[O:40])=[O:39])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of Intermediate 51 (7.51 g, 19.54 mmol) in THF (500 ml) at 0° C. was added NaH (1.172 g, 29.3 mmol) portionwise. The mixture was stirred at 0° C. for 3 hrs, then benzenesulfonyl chloride (3.70 ml, 25.4 mmol) was added and stirring was continued at r.t. overnight. The reaction mixture was quenched with sat. aqueous NH4Cl solution, and extracted with EtOAc. The organic layer was dried, filtered, and evaporated to dryness. Purification by flash chromatography (silica gel, cyclohexane/EtOAc gradient) yielded Intermediate 52.

Workup

stirringstirring
waitwas continued at r.t. overnight
customThe reaction mixture was quenched with sat. aqueous NH4Cl solution
extractionextracted with EtOAc
customThe organic layer was dried
filtrationfiltered
customevaporated to dryness
customPurification by flash chromatography (silica gel, cyclohexane/EtOAc gradient)

Sources & evidence

ORD record: ord-6a7487968c2645d0a3bad3d28c14464a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233111B2

Reaction notes

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