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4-(Tri-n-butylstannyl)thiazole → Tert-butyl 3-fluoro-4-(thiazol-4-yl)phenylcarbamate

HRID 558999
Notes
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Reaction equation

HRID 558999 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1I.C([Sn](CCCC)(CCCC)[C:22]1[N:23]=[CH:24][S:25][CH:26]=1)CCC>O1CCOCC1.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>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[C:22]1[N:23]=[CH:24][S:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 44203004Tert-butyl 3-fluoro-4-iodophenylcarbamate

Product 1

HCID 57471879Tert-butyl 3-fluoro-4-(thiazol-4-yl)phenylcarbamateYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 31275
1,4-Dioxane
Solvent

Procedure

A solution of tert-butyl 3-fluoro-4-iodophenylcarbamate (500 mg, 1.48 mmol) and 4-(tributylstannyl)thiazole (0.578 mL, 1.80 mmol) in dioxane (6 mL) was degassed with Ar before being charged with Pd(Ph3P)4 (170 mg, 0.147 mmol). It was stirred at 100 C for 34 h, then concentrated in vacuo. The residue was loaded to a flash column, eluted with 0-25% EtOAc in hexane to give tert-butyl 3-fluoro-4-(thiazol-4-yl)phenylcarbamate (270 mg). MS 295.3 (M+H)

Workup

  1. concentrationconcentrated in vacuo
  2. washeluted with 0-25% EtOAc in hexane

Sources & evidence

ORD record
ord-3861e8c8fe6c400b8f2aa0cc30c5e081
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063058B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes