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

HRID 1363063Notes

Reaction equation

HRID 1363063 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[C:15]([C:21]#N)=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1[Cl:9].I[C:24]1[C:25]2[CH:32]=[CH:31][NH:30][C:26]=2[N:27]=[CH:28][N:29]=1.C1C[O:36]CC1>C1([Mg]Cl)C=CC=CC=1.C([Mg]Cl)(C)C>[Cl:2][C:3]1[CH:4]=[C:5]([S:10]([NH:13][C:14]2[C:15]([C:21]([C:24]3[C:25]4[CH:32]=[CH:31][NH:30][C:26]=4[N:27]=[CH:28][N:29]=3)=[O:36])=[N:16][CH:17]=[C:18]([CH3:20])[CH:19]=2)(=[O:11])=[O:12])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 578708044-Iodo-7H-pyrrolo(2,3-d)pyrimidineHCID 666024953,4-dichloro-N-(2-cyano-5-methyl-pyridin-3-yl)-benzenesulfonamide sodium salt

Product 1

HCID 251712323,4-Dichloro-N-[5-methyl-2-(7H-pyrrolo[2,3-d]pyrimidine-4-carbonyl)-pyridin-3-yl]-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 178418918HCID 178418918, compoundSolventHCID 178478979HCID 178478979, compoundSolvent

Procedure

Prepared from 563 mg (1.55 mmol) of 3,4-dichloro-N-(2-cyano-5-methyl-pyridin-3-yl)-benzenesulfonamide sodium salt, 506 mg (2.01 mmol) of 97% 4-iodo-7H-pyrrolo[2,3-d]pyrimidine dissolved in 6 mL THF with 1.16 mL of 1.8 M phenylmagnesium chloride solution in THF and 1.06 mL of 2 M isopropylmagnesium chloride solution in THF added. The reaction yielded 471 mg of the final product as a yellow solid.

Workup

  1. additionadded

Sources & evidence

ORD record
ord-da2b1074b7d248c689f58c7a4770ab5d
Source dataset
uspto-grants-2011_02
Patent number
US07884110B2

Reaction notes

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