Dimethylamine → HCID 59513570, compound

HRID 1159868Notes

Reaction equation

HRID 1159868 reaction equation
[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](I)[CH3:21])[C:3]=1[OH:23].[NH:24]([CH3:26])[CH3:25]>C(Cl)Cl.CCO>[CH3:25][N:24]([CH3:26])[CH:20]([C:4]1[C:3]([OH:23])=[C:2]([F:1])[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH3:21]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 68717407HCID 68717407, compound2×

Product 1

HCID 59513570HCID 59513570, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of crude 6-fluoro-4-(1-iodoethyl)-1-(phenylsulfonyl)-1H-indol-5-ol (ca. 44.5 μmol; Intermediate 104) in CH2Cl2 (1 mL) was treated with Me2NH (159 μL of a 5.6 M solution in EtOH, 890 μmol) at rt for 1.5 h. The reaction mixture was concentrated in vacuo, the obtained residue taken up with MeOH and purified by prep. HPLC (25-55% MeCN, 50 mM NH4HCO3) to yield the title compound as an off-white solid (10.0 mg, 62% over two steps). MS (ESI+) for C18H19FN2O3S m/z 363 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by prep

Sources & evidence

ORD record
ord-81da7e9616c644f5802e975750286696
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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