Pivaloyl chloride → 2,6-Difluoro-3-(tert-butylcarbonylamino-methyl)-benzoic acid

HRID 1846111Notes

Reaction equation

HRID 1846111 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:13])=[C:5]([C:9]([F:12])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C:14](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15].FC(F)(F)C(=N[Si](C)(C)C)O[Si](C)(C)C.CSC1C2C(=CC(Br)=CC=2Br)NC=1SC>C1COCC1>[F:13][C:4]1[C:3]([CH2:2][NH:1][C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])=[CH:11][CH:10]=[C:9]([F:12])[C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 94358Bis(trimethylsilyl)trifluoroacetamideHCID 141858534,6-Dibromo-2,3-bis(methylsulfanyl)-1H-indoleHCID 584834803-(Aminomethyl)-2,6-difluorobenzoic acid

Product 1

HCID 584833392,6-Difluoro-3-(tert-butylcarbonylamino-methyl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to 44b with 3-aminomethyl-2,6-difluorobenzoic acid, Piv-Cl, BSTFA and TEA in THF. Yield: 1.2 g (77%); MS: [m+H]+=272; HPLC: Rt=1.38 min (Method MC-6)

Sources & evidence

ORD record
ord-f7cbc469eec047fc85d558065fc6414c
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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