2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1,3-thiazole → Ethyl (2R)-4-{5-fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoate

HRID 1625054Notes

Reaction equation

HRID 1625054 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]([CH:18]=[CH:19][CH:20]=2)[O:12][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)O1.[F:22][C:23]1[C:24](C2C=CC(OC[C@H]3CC[C@H](OC4CCCCO4)CC3)=CC=2)=[CH:25][C:26](=[O:42])[N:27]([CH2:29][CH2:30][C@@:31]([CH3:41])([S:37]([CH3:40])(=[O:39])=[O:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:28]=1>>[F:22][C:23]1[C:24]([C:9]2[CH:20]=[CH:19][CH:18]=[C:11]([O:12][C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[CH:10]=2)=[CH:25][C:26](=[O:42])[N:27]([CH2:29][CH2:30][C@@:31]([CH3:41])([S:37]([CH3:40])(=[O:38])=[O:39])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:28]=1

Participants

3

Reactant 2

HCID 706645942-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1,3-thiazoleHCID 178471465HCID 178471465, compound

Product 1

HCID 86670663Ethyl (2R)-4-{5-fluoro-2-oxo-4-[3-(1,3-thiazol-2-yloxy)phenyl]pyridin-1(2H)-yl}-2-methyl-2-(methylsulfonyl)butanoate

Procedure

The title compound (534 mg) was prepared as a crude brown oil from 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-1,3-thiazole (1.33 g, 4.39 mmol) and T2 (400 mg, 0.90 mmol) using a procedure analogous to that described for ethyl (2R)-4-[5-fluoro-2-oxo-4-(4-{[trans-4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]methoxy}phenyl)pyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoate, Example 18, Step D. MS (LCMS) m/z 495.2 (M+1).

Sources & evidence

ORD record
ord-57b6aa2e33ae42aaac7ef6baf616d93f
Source dataset
uspto-grants-2014_07
Patent number
US08779148B2

Reaction notes

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