HCID 86618265, compound → HCID 68717629, compound

HRID 1159870Notes

Reaction equation

HRID 1159870 reaction equation
[F:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([CH:20]=[O:21])[C:5]2[CH:6]=[CH:7][N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]=2[CH:10]=1.[CH3:24][Mg+].[Br-]>C1COCC1.C1(C)C=CC=CC=1.C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[C:4]([CH:20]([OH:21])[CH3:24])[C:3]=1[O:22][CH3:23]

Participants

5

Reactant 2

HCID 86618265HCID 86618265, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 68717629HCID 68717629, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

A solution of crude 6-fluoro-5-methoxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (72.3 mg, 217 μmol) in THF (2 mL) was treated with MeMgBr (310 μL of a 1.4 M solution in Toluene/THF, 2 eq) at rt and stirred for 20 min (50% conversion). After 20 min another 2 eq Grignard solution were added and stirring continued for 15 min. The reaction mixture was quenched with sat. NH4Cl, extracted with EtOAc (3×), the combined org. phases were washed with brine, dried and the solvent removed in vacuo to give a yellow-brownish foam (81.9 mg), 56% pure according to LC/MS. This material was purified by prep. HPLC (25-55% MeCN/50 mM NH4HCO3) to yield the title compound as an off-white solid (26.5 mg, 9% over 4 steps). MS (ESI+) for C17H16FNO4S m/z 332 (M-OH)+.

Workup

  1. additionAfter 20 min another 2 eq Grignard solution were added
  2. stirringstirring
  3. waitcontinued for 15 min
  4. customThe reaction mixture was quenched with sat. NH4Cl
  5. extractionextracted with EtOAc (3×)
  6. washphases were washed with brine
  7. customdried
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e1e80c2895a44cb39094b58373b0befa
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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