Tetrahydrofuran → 4-Methyl-N-[5-methyl-2-(7H-pyrrolo[2,3-d]pyrimidine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

HRID 1054516Notes

Reaction equation

HRID 1054516 reaction equation
C([C:3]1[C:8]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=2)(=[O:12])=[O:11])=[CH:7][C:6]([CH3:24])=[CH:5][N:4]=1)#N.[H-].[Na+].I[C:28]1[C:29]2[CH:36]=[CH:35][NH:34][C:30]=2[N:31]=[CH:32][N:33]=1.C1C[O:40][CH2:39]C1>C1([Mg]Cl)C=CC=CC=1.C([Mg]Cl)(C)C>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([NH:9][C:8]2[C:3]([C:39]([C:28]3[C:29]4[CH:36]=[CH:35][NH:34][C:30]=4[N:31]=[CH:32][N:33]=3)=[O:40])=[N:4][CH:5]=[C:6]([CH3:24])[CH:7]=2)(=[O:12])=[O:11])=[CH:14][C:15]=1[C:20]([F:21])([F:23])[F:22]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran4×HCID 24758Sodium hydrideHCID 578708044-Iodo-7H-pyrrolo(2,3-d)pyrimidineHCID 57870821N-(2-cyano-5-methyl-pyridin-3-yl)-4-methyl-3-trifluoromethyl-benzenesulfonamide

Product 1

HCID 251712314-Methyl-N-[5-methyl-2-(7H-pyrrolo[2,3-d]pyrimidine-4-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 178418918HCID 178418918, compoundSolventHCID 178478979HCID 178478979, compoundSolvent

Procedure

Prepared from 496 mg (1.40 mmol) of N-(2-cyano-5-methyl-pyridin-3-yl)-4-methyl-3-trifluoromethyl-benzenesulfonamide and 70 mg (1.75 mmol) of 60% sodium hydride in 2 mL THF. The Grignard solution was prepared from 467 mg (1.82 mmol) of 95% 4-iodo-7H-pyrrolo[2,3-d]pyrimidine dissolved in 5 mL THF with 0.98 mL of 2 M phenylmagnesium chloride solution in THF and 0.98 mL of 2 M isopropylmagnesium chloride solution in THF added. The reaction yielded 340 mg of the final product as a yellow solid.

Workup

  1. additionadded

Sources & evidence

ORD record
ord-dea48ebe9b8d4e63b83ffd41fcf397fc
Source dataset
uspto-grants-2016_07
Patent number
US09394307B2

Reaction notes

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