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Sodium Carbonate → Methyl2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881718
Notes
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Reaction equation

HRID 881718 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([C:15]34[CH2:22][CH2:21][C:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:19][CH2:20]3)[O:17][CH2:16]4)=[CH:11][CH:10]=2)O1.Br[C:30]1[N:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:27][O:26][C:24](=[O:25])[CH2:23][C:18]12[CH2:21][CH2:22][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:30]4[CH:31]=[CH:32][C:33]([NH2:36])=[CH:34][N:35]=4)=[CH:14][CH:13]=3)([CH2:20][CH2:19]1)[CH2:16][O:17]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6428116-Bromopyridin-3-amineHCID 86700826Methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Product 1

HCID 86700825Methyl2-(4-(4-(5-aminopyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetateYield 131%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

To a microwave vial containing methyl 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate (100 mg, 0.26 mmol), 6-bromopyridin-3-amine (49 mg, 0.28 mmol) and Pd2(PPh3)4 (60 mg, 0.05 mmol) was added 1,4-dioxane (1.3 ml) at room temperature. 2N sodium carbonate (0.39 ml, 0.78 mmol) was added and the mixture was subjected to microwave radiation at 120° C. for 50 minutes. The resulting mixture was concentrated to dryness and taken up in EtOAc, the slurry was dried over sodium sulfate and filtered through a pad of celite. The filtrate was concentrated and purified by column chromatography to afford the title compound (120 mg, 65% yield). LC/MS, ESI-MS(+): 353.4, RT: 1.12 (Condition E).

Workup

  1. customat 120° C.
  2. customfor 50 minutes
  3. concentrationThe resulting mixture was concentrated to dryness
  4. dry with materialthe slurry was dried over sodium sulfate
  5. filtrationfiltered through a pad of celite
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-c383c490c51440139d42ba3711ecb3d4
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08993619B2

Reaction notes

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