Dimethylformamide → HCID 22467205, compound

HRID 369348Notes

Reaction equation

HRID 369348 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:12]([C:28]3[CH:36]=[C:35]([O:37][CH3:38])[C:31]4[O:32][CH2:33][O:34][C:30]=4[CH:29]=3)[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=3[O:26][CH3:27])(=[O:18])=[O:17])=[O:14])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.CN(C)[CH:41]=[O:42]>CCCCCC.O1CCCC1>[CH:41]([C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:12]([C:28]3[CH:36]=[C:35]([O:37][CH3:38])[C:31]4[O:32][CH2:33][O:34][C:30]=4[CH:29]=3)[C:13]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][C:20]=3[O:26][CH3:27])(=[O:18])=[O:17])=[O:14])=[CH:7][N:8]2[CH3:11])=[CH:4][CH:3]=1)=[O:42]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 22467218HCID 22467218, compound

Product 1

HCID 22467205HCID 22467205, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Butylithium (0.8 ml of 2.5M solution in hexane) was added to a stirred solution of 6-bromo-3-{1-(7-methoxy-1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-1H-indole (from Example 92, 400 mg, 0.67 mmol) in anhydrous tetrahydrofuran at -75° C. under a nitrogen atmosphere. After 30 minutes dimethylformamide (0.15 ml) was added to the orange solution, and after a further 30 minutes the mixture was allowed to warm at 0° C. before quenching with excess 1N hydrochloric acid. Ethyl acetate was added and the organic layer was separated and washed with water. The organic layer was dried (magnesium sulphate), and the solvents removed in vacuo. The residue was flash chromatographed using 1% methanol in dichloromethane as eluant, and the product was crystallised from dichloromethane and diethyl ether mixture to give the title compound (187 mg).

Workup

  1. custombefore quenching with excess 1N hydrochloric acid
  2. additionEthyl acetate was added
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialThe organic layer was dried (magnesium sulphate)
  6. customthe solvents removed in vacuo
  7. customchromatographed
  8. customthe product was crystallised from dichloromethane and diethyl ether mixture

Sources & evidence

ORD record
ord-f337c11b5f974092a41cd3621c86f88f
Source dataset
uspto-grants-2000_10
Patent number
US06136843

Reaction notes

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