(Diethylamino)sulfur trifluoride → HCID 70564766, compound

HRID 1427299Notes

Reaction equation

HRID 1427299 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:11][CH2:12][CH2:13]O)[CH2:9][CH3:10])=[CH:4][CH:3]=1.CCN(S(F)(F)[F:35])CC>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:15]2[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16]2)([CH2:11][CH2:12][CH2:13][F:35])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 70564858HCID 70564858, compound

Product 1

HCID 70564766HCID 70564766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(3-(4-chlorophenyl)-6-hydroxyhexan-3-yl)-1H-indol-4-yl)methanesulfonamide (21 mg, 0.05 mmol), as described in Example 45 Step A, in dichloromethane (2 mL) was added DAST (16 mg, 0.1 mmol) at −78° C. The mixture was gradually warmed to room temperature and stirred for 3 h, then quenched with methanol (0.5 mL). The crude product was purified by PREP-TLC eluting with PE/EA (2/1, v/v) to obtain the title compound as colorless oil. LC/MS m/z=444.7[M+Na]+.

Workup

  1. customquenched with methanol (0.5 mL)
  2. customThe crude product was purified
  3. washby PREP-TLC eluting with PE/EA (2/1

Sources & evidence

ORD record
ord-1ddb61978db34dd7b6b2afff74510584
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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