3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → (S)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(pyridin-3-yl)-5H-spiro[thiazole-4,9'-xanthen]-2-amine

HRID 336023Notes

Reaction equation

HRID 336023 reaction equation
[NH2:1][C:2]1[S:3][CH2:4][C@@:5]2([N:22]=1)[C:18]1[CH:17]=[C:16](O)[CH:15]=[C:14]([F:20])[C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8](Br)=[CH:9][CH:10]=1.[F:23][C:24]1[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][N:25]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[F:20][C:14]1[C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:29]4[C:24]([F:23])=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:9][CH:10]=3)[C@@:5]3([CH2:4][S:3][C:2]([NH2:1])=[N:22]3)[C:18]=2[CH:17]=[C:16]([C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)[CH:15]=1

Participants

4

Reactant 3

HCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 27832702-Fluoropyridine-3-boronic acidHCID 67383112(S)-2-amino-7'-bromo-4'-fluoro-5H-spiro[thiazole-4,9'-xanthen]-2'-ol

Product 1

HCID 53464382(S)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-2'-(pyridin-3-yl)-5H-spiro[thiazole-4,9'-xanthen]-2-amine

Procedure

The titled compound was synthesized by stpes analogous to those described in method AA8 above, but using (S)-2-amino-7′-bromo-4′-fluoro-5H-spiro[thiazole-4,9′-xanthen]-2′-ol (prepared as described in Method BB26 and Example 2 but using 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one), 2-fluoropyridin-3-ylboronic acid and 3-pyridineboronic acid pinacol ester. MS m/z=459.0 [M+H]+.

Sources & evidence

ORD record
ord-70019c2c3a7e4128836f69df2512c2e4
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

Loading…