4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane → (S)-2-[5-(3-Amino-4-isopropenyl-6-methoxy-5-trifluoromethyl-pyridin-2-yl)-[1,3,4]oxadiazol-2-yl]-1,1,1-trifluoro-propan-2-ol

HRID 574221Notes

Reaction equation

HRID 574221 reaction equation
[NH2:1][C:2]1[C:3]([C:16]2[O:20][C:19]([C@@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[N:18][N:17]=2)=[N:4][C:5]([O:14][CH3:15])=[C:6]([C:10]([F:13])([F:12])[F:11])[C:7]=1[CH:8]=[CH2:9].[CH3:28]C1(C)C(C)(C)OB(C(C)=C)O1>>[NH2:1][C:2]1[C:3]([C:16]2[O:20][C:19]([C@@:21]([OH:27])([CH3:26])[C:22]([F:25])([F:24])[F:23])=[N:18][N:17]=2)=[N:4][C:5]([O:14][CH3:15])=[C:6]([C:10]([F:12])([F:13])[F:11])[C:7]=1[C:8]([CH3:28])=[CH2:9]

Participants

3

Reactant 2

HCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 86729605(S)-2-(5-(3-Amino-6-methoxy-5-(trifluoromethyl)-4-vinylpyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol

Product 1

HCID 71515816(S)-2-[5-(3-Amino-4-isopropenyl-6-methoxy-5-trifluoromethyl-pyridin-2-yl)-[1,3,4]oxadiazol-2-yl]-1,1,1-trifluoro-propan-2-ol

Procedure

The title compound was prepared analogously to (S)-2-(5-(3-Amino-6-methoxy-5-(trifluoromethyl)-4-vinylpyridin-2-yl)-1,3,4-oxadiazol-2-yl)-1,1,1-trifluoropropan-2-ol (Example 14.0 step 1) by replacing 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane with 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane;

Sources & evidence

ORD record
ord-853b89d3ef6b40198cb46431cd7d8a2e
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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