Cesium carbonate → 7-(2-Fluoro-4-iodo-phenylamino)-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

HRID 1259435Notes

Reaction equation

HRID 1259435 reaction equation
[N+:1]([C:4]1[C:9](OS(C(F)(F)F)(=O)=O)=[CH:8][C:7](=[O:18])[N:6]2[CH2:19][CH2:20][S:21][C:5]=12)([O-:3])=[O:2].[F:22][C:23]1[CH:28]=[C:27]([I:29])[CH:26]=[CH:25][C:24]=1[NH2:30].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:22][C:23]1[CH:28]=[C:27]([I:29])[CH:26]=[CH:25][C:24]=1[NH:30][C:9]1[C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[S:21][CH2:20][CH2:19][N:6]2[C:7](=[O:18])[CH:8]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 1856942-Fluoro-4-iodoanilineHCID 634876Binap, (A+-)-HCID 58380532Methanesulfonic acid, 1,1,1-trifluoro-, 2,3-dihydro-8-nitro-5-oxo-5H-thiazolo[3,2-a]pyridin-7-yl ester

Product 1

HCID 583805547-(2-Fluoro-4-iodo-phenylamino)-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-oneYield 12.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

Trifluoro-methanesulfonic acid 8-nitro-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-7-yl ester (0.6 g, 1.7 mmol) was reacted with 2-fluoro-4-iodo-phenylamine (0.45 g, 1.9 mmol), Pd(OAc)2 (38 mg, 0.17 mmol), BINAP (0.1 g, 0.17 mmol) and cesium carbonate (0.84 g, 2.6 mmol) in toluene (20 mL) at reflux for 3 hours to afford the crude product. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 90 mg of the product (12% yield).

Workup

  1. temperatureat reflux for 3 hours
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-fafa60bef2484d77bd9375886da8a00b
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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