HCID 22663271, compound → HCID 22663214, compound

HRID 2054477Notes

Reaction equation

HRID 2054477 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[NH:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:30]=[O:31])=[CH:16][N:17]2[S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:13][CH:12]=1)=[O:10].[CH3:33][Mg]Br>O1CCCC1.C(OCC)C>[Cl:32][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:30]([OH:31])[CH3:33])=[CH:16][N:17]2[S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 22663271HCID 22663271, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22663214HCID 22663214, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of N-(3,5-dichloro-pyridin-4-yl)-3-formyl-1-(toluene-4-sulphonyl)-1H-indole-6-carboxamide (0.1 g, Example 17) in tetrahydofuran (3 ml), at 0° C., was treated with a solution of methylmagnesium bromide in diethyl ether (0.11 ml, 3M). The mixture was allowed to warm to room temperature then stirred for 2 hours. The reaction mixture was quenched with water (15 ml) and then extracted with ethyl acetate (15 ml). The organic extract was dried over sodium sulphate then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (2:1, v/v) to yield the title compound (68 mg) as a white solid, m.p. 206-211° C. [Elemental analysis:—C, 55.07; H, 4.00; N, 7.92%. Calculated for C23H19Cl2N3O4S:—C, 54.77; H, 3.80; N, 8.33%].

Workup

  1. customThe reaction mixture was quenched with water (15 ml)
  2. extractionextracted with ethyl acetate (15 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulphate
  5. customthen evaporated
  6. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (2:1

Sources & evidence

ORD record
ord-385552b5f8bf4a16a49fab041c947b7d
Source dataset
uspto-grants-2008_02
Patent number
US07329675B2

Reaction notes

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