Dichloromethane → HCID 11619112, compound

HRID 1724017Notes

Reaction equation

[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:14][CH:15]=2)[CH:10]=C1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Cl:34])C(=O)C1.[CH2:35]([Cl:37])Cl>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:14][CH:15]=2)[C:10]([Cl:34])=[C:35]1[Cl:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 31398Chlorosuccinimide

HCID 11696424HCID 11696424, compound

Product 1

HCID 11619112HCID 11619112, compoundYield 21%

Procedure

A solution of 400 mg (1.07 mmol) of 2-(1-benzyl-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (example 16) in 2 mL CH2Cl2 was treated portionwise with 286 mg (2.14 mmol) of NCS and stirred at RT for 10 hrs. Evaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 3:1 to 1:1 yielded 100 mg (21%) of 2-(1-benzyl-2,3-dichloro-1H-indol-5-yl)-1,1,1,3,3,3-hexafluoro-propan-2-ol, light brown oil, MS: 441 (M−H)−, 2Cl.

Workup

customEvaporation of the solvent and column chromatography on silica gel with n-heptane/EtOAc 3:1 to 1:1

Sources & evidence

ORD record: ord-68b762636e7147188949e4c4ac70aeac
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485652B2

Reaction notes

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