2-(Tributylstannyl)pyrazine → (S)-2'-(3,6-dihydro-2H-pyran-4-yl)-4'-fluoro-7'-(pyrazin-2-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335998Notes

Reaction equation

HRID 335998 reaction equation
[NH2:1][C:2]1[O:3][CH2:4][C@@:5]2([N:22]=1)[C:18]1[CH:17]=[C:16](Br)[CH:15]=[C:14]([F:20])[C:13]=1[O:12][C:11]1[C:6]2=[CH:7][C:8](O)=[CH:9][CH:10]=1.[O:23]1[CH2:28][CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH2:25][CH2:24]1.C([Sn](CCCC)(CCCC)[C:43]1[CH:48]=[N:47][CH:46]=[CH:45][N:44]=1)CCC>>[O:23]1[CH2:28][CH:27]=[C:26]([C:16]2[CH:15]=[C:14]([F:20])[C:13]3[O:12][C:11]4[C:6](=[CH:7][C:8]([C:43]5[CH:48]=[N:47][CH:46]=[CH:45][N:44]=5)=[CH:9][CH:10]=4)[C@@:5]4([CH2:4][O:3][C:2]([NH2:1])=[N:22]4)[C:18]=3[CH:17]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 27373162-(Tributylstannyl)pyrazineHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 67383727(S)-2-amino-2'-bromo-4'-fluoro-5H-spiro[oxazole-4,9'-xanthen]-7'-ol

Product 1

HCID 53465070(S)-2'-(3,6-dihydro-2H-pyran-4-yl)-4'-fluoro-7'-(pyrazin-2-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Procedure

The titled compound was synthesized by steps analogous to those described in method AA22 above, but using (S)-2-amino-2′-bromo-4′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-7′-ol (prepared as described in Method BB40 but using 4-bromo-2-fluorophenol and 2-bromo-5-methoxybenzoic acid), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and 2-(tributylstannyl)pyrazine

Sources & evidence

ORD record
ord-80e5e62425c549e28277827fb26180c0
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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