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Water → Methyl 2-(4-(4'-(2-ethyl-4-methyloxazole-5-carboxamido)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881735
Notes
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Reaction equation

HRID 881735 reaction equation
[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15](B3OC(C)(C)C(C)(C)O3)=[CH:14][CH:13]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2].Br[C:28]1[CH:33]=[CH:32][C:31]([C:34]23[CH2:41][CH2:40][C:37]([CH2:42][C:43]([O:45][CH3:46])=[O:44])([CH2:38][CH2:39]2)[O:36][CH2:35]3)=[CH:30][CH:29]=1.O.[F-].[Cs+]>O1CCOCC1.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH2:1]([C:3]1[O:4][C:5]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:28]3[CH:29]=[CH:30][C:31]([C:34]45[CH2:39][CH2:38][C:37]([CH2:42][C:43]([O:45][CH3:46])=[O:44])([CH2:40][CH2:41]4)[O:36][CH2:35]5)=[CH:32][CH:33]=3)=[CH:16][CH:17]=2)=[O:10])=[C:6]([CH3:8])[N:7]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 86700823Methyl 2-(4-(4-bromophenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateHCID 867008392-ethyl-4-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole-5-carboxamide

Product 1

HCID 86700840Methyl 2-(4-(4'-(2-ethyl-4-methyloxazole-5-carboxamido)-[1,1'-biphenyl]-4-yl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate
Yield 58%

Reagents, catalysts & solvents 2

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-ethyl-4-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole-5-carboxamide (200 mg, 0.561 mmol) and methyl 2-(4-(4-bromophenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (190 mg, 0.561 mmol) in dioxane (3 ml) was added H2O (0.33 ml). CsF (256 mg, 1.684 mmol) and Pd(amphos)Cl2 (39.8 mg, 0.056 mmol) were then added and the mixture was degassed before being heated at 90° C. for overnight. The reaction mixture was then cooled to room temperature and directly purified by column chromatography to afford the title compound as white solid after drying (159 mg, 58% yield). LC/MS, ESI-MS(+): 489.0, RT: 1.40 (Condition E).

Workup

  1. customthe mixture was degassed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customdirectly purified by column chromatography

Sources & evidence

ORD record
ord-70f9ecb5f4e2449cb0ad6a3cb5142a91
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993619B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes