Dimethylformamide → (S)-2-amino-4'-fluoro-7'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2'-ol

HRID 335733Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[O:9][CH2:10][C@@:11]2([N:28]=1)[C:24]1[CH:23]=[C:22]([OH:25])[CH:21]=[C:20]([F:26])[C:19]=1[O:18][C:17]1[C:12]2=[CH:13][C:14](Br)=[CH:15][CH:16]=1.[F:29][C:30]1[C:35](B(O)O)=[CH:34][CH:33]=[CH:32][N:31]=1.CN(C=O)C>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:7][C:8]1[O:9][CH2:10][C@@:11]2([N:28]=1)[C:24]1[CH:23]=[C:22]([OH:25])[CH:21]=[C:20]([F:26])[C:19]=1[O:18][C:17]1[C:12]2=[CH:13][C:14]([C:35]2[C:30]([F:29])=[N:31][CH:32]=[CH:33][CH:34]=2)=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A RBF was charged with sodium carbonate (2 M, 2 mL), tetrakis(triphenylphosphine)palladium (0.237 g, 0.205 mmol), (S)-2-amino-7′-bromo-4′-fluoro-5H-spiro[oxazole-4,9′-xanthen]-2′-ol (0.75 g, 2.054 mmol), and 2-fluoro-3-pyridineboronic acid (0.579 g, 4.11 mmol) and DMF (5 ml). The solution was heated at 85° C. overnight. The solution was diluted with water (25 ml) and filtered. The solids were triturated with methanol and dried under vacuum to afford (S)-2-amino-4′-fluoro-7′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2′-ol as a tan solid.

Workup

filtrationfiltered
customThe solids were triturated with methanol
customdried under vacuum

Sources & evidence

ORD record: ord-3e919b83f279409999925a4fb449a977
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

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