Toluene → tert-butyl 5-(1-methyl-3-fluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbamate

HRID 1699761Notes

Reaction equation

HRID 1699761 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:11][C:10](C(O)=O)=[CH:9][CH:8]=2)=[CH:5][C:4]([C:15]([F:18])(F)F)=[N:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C(C1C=CC=CC=1[N:40]([CH2:43]C)CC)C.C1(C)C=CC=CC=1.[C:56]([OH:60])([CH3:59])([CH3:58])[CH3:57]>>[CH3:1][N:2]1[C:6]([C:7]2[S:11][C:10]([NH:40][C:43]([O:60][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:26])=[CH:9][CH:8]=2)=[CH:5][C:4]([CH2:15][F:18])=[N:3]1

Participants

6

Reactant 5

HCID 1140TolueneHCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 27756685-(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)-2-thiophenecarboxylic acidHCID 18366426N,N,2-Triethylaniline

Product 1

HCID 18369591tert-butyl 5-(1-methyl-3-fluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbamate

Conditions

Temperature
50 °C

Procedure

A mixture of 5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid, diphenylphosphoryl azide, triethylamline and toluene was stirred at 50° C. for 30 minutes. Then, tert-butanol was added to the reaction solution. After stirring at 80° C. for 5 hours, it was subjected to purification in the usual way to give tert-butyl 5-(1-methyl-3-fluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbamate as light yellow crystals.

Workup

  1. stirringAfter stirring at 80° C. for 5 hours
  2. customit was subjected to purification in the usual way

Sources & evidence

ORD record
ord-72df664ae8ac4d13863834696bd4ed86
Source dataset
uspto-grants-2002_02
Patent number
US06348480B1

Reaction notes

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