2-Pyridinamine, 5-iodo- → Methyl 2-(4-(4-(6-aminopyridin-3-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

HRID 881723Notes

Reaction equation

HRID 881723 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.I[C:30]1[CH:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=1>>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:9]2[CH:10]=[CH:11][C:12]([C:15]34[CH2:20][CH2:19][C:18]([CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:21][CH2:22]3)[O:17][CH2:16]4)=[CH:13][CH:14]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 885792-Pyridinamine, 5-iodo-HCID 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 86700830Methyl 2-(4-(4-(6-aminopyridin-3-yl)phenyl)-2-oxabicyclo[2.2.2]octan-1-yl)acetate

Procedure

The title compound was prepared analogous to Example 4, Step 1 starting from 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 (200 mg, 0.52 mmol) and 5-iodopyridin-2-amine (137 mg, 0.62 mmol). The reaction was performed at 80° C. for overnight. After workup and column purification afforded the title compound as off-white solid after drying (133 mg, 58% yield). LC/MS, ESI-MS(+):353.3, RT: 1.12 (Condition E).

Workup

  1. customAfter workup and column purification

Sources & evidence

ORD record
ord-5e23f29934ae436ea49272bcf2ef8e9b
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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