Potassium Carbonate → N-[4-({3-Cyclopropyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide

HRID 2192165Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[N:4]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:39]1(B(O)O)[CH2:41][CH2:40]1>CN(C=O)C.ClCCl.CO>[CH:39]1([C:2]2[C:10]3[C:5](=[N:6][CH:7]=[CH:8][C:9]=3[O:11][C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=3[F:22])[N:4]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:3]=2)[CH2:41][CH2:40]1

Participants

Conditions

Temperature: 110 °C

Procedure

500 mg (0.96 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide and 400 mg (2.89 mmol) of potassium carbonate are suspended in DMF (5 ml). The solution is degassed and vented with argon. 39 mg (0.05 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride/methylene dichloride complex and 207 mg (2.41 mmol) of cyclopropylboronic acid (Wallace, Debra J.; Chen, Cheng-yl; Tetrahedron Lett. 2002, 43(39), 6987-6990) are then added. The mixture is heated at 110° C. overnight. The reaction mixture is then dissolved in dichloromethane/methanol 10:1 and filtered through an Extrelut cartridge. The filtrate is concentrated under reduced pressure and the crude product is purified by preparative HPLC.

Workup

customThe solution is degassed
filtrationfiltered through an Extrelut cartridge
concentrationThe filtrate is concentrated under reduced pressure
customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record: ord-71cbb23083894701abca66a511dd8759
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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