4-Toluenesulfonyl chloride → HCID 59540985, compound

HRID 1677369Notes

Reaction equation

HRID 1677369 reaction equation
BrC1N=C2C=CNC2=NC=1.COC1C=C(B(O)O)C=CC=1OC.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:34]2[N:35]=[C:36]3[C:42]([I:43])=[CH:41][NH:40][C:37]3=[N:38][CH:39]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].[H-].[Na+].[S:46](Cl)([C:49]1[CH:55]=[CH:54][C:52]([CH3:53])=[CH:51][CH:50]=1)(=[O:48])=[O:47]>C1COCC1.CCOC(C)=O.O>[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:34]2[N:35]=[C:36]3[C:42]([I:43])=[CH:41][NH:40][C:37]3=[N:38][CH:39]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:34]2[N:35]=[C:36]3[C:42]([I:43])=[CH:41][N:40]([S:46]([C:49]4[CH:55]=[CH:54][C:52]([CH3:53])=[CH:51][CH:50]=4)(=[O:48])=[O:47])[C:37]3=[N:38][CH:39]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33]

Participants

10

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 27347023,4-Dimethoxyphenylboronic acidHCID 250673082-bromo-5H-pyrrolo[2,3-b]pyrazineHCID 59540677HCID 59540677, compound

Product 2

HCID 59540677HCID 59540677, compoundHCID 59540985HCID 59540985, compoundYield 121%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3,4-Dimethoxy-phenyl)-7-iodo-5H-pyrrolo[2,3-b]pyrazine was prepared starting from 2-bromo-5H-pyrrolo[2,3-b]pyrazine and 3,4-dimethoxyphenylboronic acid. To a 0° C. solution of 2-(3,4-dimethoxy-phenyl)-7-iodo-5H-pyrrolo[2,3-b]pyrazine (821 mg, 2.1 mmol) in THF (20 mL) was added NaH (55% dispersion in mineral oil, 168 mg, 3.85 mmol) portionwise and the resultant mixture was stirred for 15 min, treated with TsCl (736 mg, 3.85 mmol), stirred overnight at room temperature, and poured into water and EtOAc. A yellow solid precipitated and the heterogeneous biphasic mixture was filtered to afford 680 mg (39%) of 2-(3,4-dimethoxy-phenyl)-7-iodo-5-(toluene-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazine as a yellow solid.

Workup

  1. customA yellow solid precipitated
  2. filtrationthe heterogeneous biphasic mixture was filtered

Sources & evidence

ORD record
ord-34228fa70d9f4a37ad2d2ce42415f3e9
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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