Boron trifluoride → HCID 22663364, compound

HRID 380400Notes

Reaction equation

HRID 380400 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:33])[C:7]=1[NH:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:30](O)[CH3:31])=[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].C([SiH](CC)CC)C.B(F)(F)F>ClCCl>[Cl:33][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]([CH2:30][CH3:31])=[CH:16][N:17]2[S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:21])=[O:22])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 22663214HCID 22663214, compound

Product 1

HCID 22663364HCID 22663364, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of N-(3,5-dichloro-pyridin-4-yl)-3-(1-hydroxyethyl)-1-(toluene-4-sulphonyl)-1H-indole-6-carboxamide [0.06 g, Example 16(a)] in dichloromethane (2 ml), under nitrogen and at 0° C., was treated with triethylsilane (0.028 g,) and boron trifluoride dietherate (0.015 ml). The mixture was allowed to warm to room temperature and then stirred at this temperature for 3 hours. The solution was partitioned between ethyl acetate (15 ml) and saturated sodium bicarbonate solution (15 ml). The organic layer 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 (gradient elution, 1:3 to 2:1, v/v) to give the title compound (22 mg) as a white solid, m.p. 147-149° C. [Elemental analysis:—C,56.69; H,4.04; N,8.15%. Calculated for C23H19Cl2N3O3S:—C,56.56; H,3.92; N,8.60%].

Workup

  1. customThe solution was partitioned between ethyl acetate (15 ml) and saturated sodium bicarbonate solution (15 ml)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customthen evaporated
  4. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (
  5. washgradient elution, 1:3 to 2:1

Sources & evidence

ORD record
ord-f8a8d78718774fdd8874f8b2b7b0de07
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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