Cesium carbonate → Methyl 3-[[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-piperidyl]-2-fluoro-benzoyl]amino]-2,4-dimethyl-benzoate

HRID 239929Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([F:23])=[C:6]([CH:22]=1)[C:7]([NH:9][C:10]1[C:11]([CH3:21])=[C:12]([CH:17]=[CH:18][C:19]=1[CH3:20])[C:13]([O:15][CH3:16])=[O:14])=[O:8].[C:24]([Si:28]([CH3:38])([CH3:37])[O:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][NH:33][CH2:32]1)([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[Cs+].[Cs+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:28]([O:29][CH2:30][CH:31]1[CH2:36][CH2:35][CH2:34][N:33]([C:2]2[CH:3]=[CH:4][C:5]([F:23])=[C:6]([CH:22]=2)[C:7]([NH:9][C:10]2[C:11]([CH3:21])=[C:12]([CH:17]=[CH:18][C:19]=2[CH3:20])[C:13]([O:15][CH3:16])=[O:14])=[O:8])[CH2:32]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:38])[CH3:37]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of methyl 3-[(5-bromo-2-fluoro-benzoyl)amino]-2,4-dimethyl-benzoate (0.7 g, 1.84 mmol), tert-butyl-dimethyl-(3-piperidylmethoxy)silane (2.53 g, 11.03 mmol, see preparation 14) and Cs2CO3 (1.81 g, 5.50 mmol) in 1,4-dioxane (15 ml) is added Pd2(dba)3 (0.168 g, 0.184 mol) followed by S-Phos (0.075 g, 0.184 mol). The reaction mixture is purged with nitrogen for 5 minutes and then heated at 120° C. After 6 hours, the reaction mixture is concentrated under reduced pressure and residue is carried forward without further purification.

Workup

customThe reaction mixture is purged with nitrogen for 5 minutes
concentrationthe reaction mixture is concentrated under reduced pressure and residue
customis carried forward without further purification

Sources & evidence

ORD record: ord-2bbfaa9864a642f4985f720bb414afcb
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642768B2

Reaction notes

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