Potassium Phosphate, Tribasic → 7-(2-Fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

HRID 1259418Notes

Reaction equation

HRID 1259418 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][S:11][C:5]2=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1OS(C(F)(F)F)(=O)=O.[F:23][C:24]1[CH:29]=[C:28]([Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:27]=[CH:26][C:25]=1[NH2:34].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[F:23][C:24]1[CH:29]=[C:28]([Si:30]([CH3:32])([CH3:31])[CH3:33])[CH:27]=[CH:26][C:25]=1[NH:34][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]2[S:11][CH2:10][CH2:9][N:6]2[C:7](=[O:8])[C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 58380549Trifluoro-methanesulfonic acid 6-methyl-8-nitro-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-7-yl esterHCID 595965992-Fluoro-4-(trimethylsilyl)aniline

Product 1

HCID 583805727-(2-Fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-oneYield 76.2%

Reagents, catalysts & solvents 2

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 1140TolueneSolvent

Procedure

Trifluoro-methanesulfonic acid 6-methyl-8-nitro-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-7-yl ester (0.9 g, 2.5 mmol) was reacted with 2-fluoro-4-trimethylsilanyl-phenylamine (0.5 g, 2.75 mmol), Pd(dba)3 (138 mg, 0.15 mmol), potassium phosphate (0.7 g, 3.75 mmol) and xantphos (87 mg, 0.15 mmol) in toluene (30 mL) at 110° C. for 3 hours to afford the crude product. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 0.75 g of the product (76% yield).

Workup

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

Sources & evidence

ORD record
ord-93da8126537c4b27af2f003e2d4ac06e
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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