4-Toluenesulfonyl chloride → 6-(2-Chloro-5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine

HRID 1765566Notes

Reaction equation

HRID 1765566 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[NH:21][C:16]2=[N:17][CH:18]=[CH:19][N:20]=[C:15]2[CH:14]=1.C([Li])CCC.C1(C)C=CC(S([Cl:36])(=O)=O)=CC=1>COC(OC)(O)C>[Cl:36][C:7]1[N:8]([CH3:12])[C:9]2[C:5]([C:6]=1[C:13]1[NH:21][C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[CH:14]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 98604486-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazineHCID 178418339Butyllithium

Product 1

HCID 98364246-(2-Chloro-5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazineYield 40%

Reagents, catalysts & solvents 1

HCID 184133611,1-Dimethoxyethan-1-olSolvent

Procedure

A solution of 6-(5-methoxy-1-methyl-1H-indol-3-yl)-5H-pyrrolo[2,3-b]pyrazine [100 mg, Example 1(a)] in dimethoxy ethanol (25 mL), cooled to −78° C., was treated with a solution of n-butyllithium in hexanes (172 μl, 2.5M). After stirring for 30 minutes the mixture was treated with 4-toluenesulfonyl chloride (82 mg) then allowed to warm slowly to ambient temperature and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (19:1, v/v) to give the title compound (45 mg) as a black solid. MS: 313 (MH+). 1H NMR [(CD3)2SO]: δ 12.20 (1H, s); 8.39 (1H, d, J=3 Hz); 8.21 (1H, d, J=3 Hz); 7.54 (1H, d, J=9 Hz); 7.30 (1H, d, J=2 Hz); 6.96 (1H, dd, J=9 and 2 Hz); 6.84 (1H, d, J=2 Hz); 3.82 (3H, s); 3.81 (3H, s).

Workup

  1. customevaporated
  2. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (19:1

Sources & evidence

ORD record
ord-36f5442a87f14e4aadc4cb4299c10483
Source dataset
uspto-grants-2007_06
Patent number
US07227020B2

Reaction notes

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