Potassium tert-butoxide → N-[3-(6-Bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide

HRID 589522Notes

Reaction equation

C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[C:20]([CH3:38])=[C:21]([NH:25][C:26](=[O:37])[C:27]5[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=5)[CH:22]=[CH:23][CH:24]=4)[C:13]=3[CH:12]=[C:11]2[Br:39])(=O)=O)C=CC=CC=1.CC([O-])(C)C.[K+]>C1COCC1>[Br:39][C:11]1[NH:10][C:14]2[N:15]=[CH:16][N:17]=[C:18]([C:19]3[C:20]([CH3:38])=[C:21]([NH:25][C:26](=[O:37])[C:27]4[CH:32]=[CH:31][C:30]([C:33]([CH3:35])([CH3:36])[CH3:34])=[CH:29][CH:28]=4)[CH:22]=[CH:23][CH:24]=3)[C:13]=2[CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of Intermediate 53 (3.82 g, 6.33 mmol) in THF (64 ml) was added a solution of potassium tert-butylate in THF (1 M, 9.49 ml, 9.49 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hr, then an additional solution of potassium tert-butylate in THF (1 M, 2.00 ml, 2.00 mmol) was added and stirring was continued for an additional 1 hr. The reaction was quenched by addition of sat. aqueous NaHCO3 solution, and the mixture was extracted with EtOAc. The organic layer was dried, filtered, and evaporated to dryness. Purification by flash chromatography (silica gel, cyclohexane/EtOAc gradient) yielded Intermediate 54.

Workup

stirringstirring
waitwas continued for an additional 1 hr
customThe reaction was quenched by addition of sat. aqueous NaHCO3 solution
extractionthe mixture was extracted 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-f5af4c6fd61843bc9cddbf6e5162bf3f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233111B2

Reaction notes

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