2-Mercaptoethanol → HCID 86597707, compound

HRID 547819Notes

Reaction equation

HRID 547819 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:40])([CH3:39])[C:14]([N:16]([C:18]2[C:19]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[CH3:38])=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]3)=[N:22][CH:23]=2)[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[SH:43][CH2:44][CH2:45]O.B(F)(F)F.CCOCC>ClCCl>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:40])[C:14]([N:16]([C:18]2[CH:23]=[N:22][C:21]([N:24]3[CH2:29][CH2:28][C:27]4([O:30][CH2:45][CH2:44][S:43]4)[CH2:26][CH2:25]3)=[CH:20][C:19]=2[C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=2[CH3:38])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 8000Boron trifluoride etherateHCID 86597708HCID 86597708, compound

Product 1

HCID 86597707HCID 86597707, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.20 g (0.34 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4′-(4-fluoro-2-methyl-phenyl)-4-oxo-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl]-N-methyl-isobutyramide in 5 ml dichloromethane were added 0.03 g (0.4 mmol) 2-mercaptoethanol and 0.11 g (0.34 mmol) boron trifluoride etherate at 0° C. After 1 h the reaction mixture was allowed to warm to room temperature and stirred over night. Dilution with a 2 N aqueous sodium hydroxide solution was followed by extraction with 3 portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 0.22 g (98%) of the title compound as a white solid.

Workup

  1. extractionDilution with a 2 N aqueous sodium hydroxide solution was followed by extraction with 3 portions of dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17f63cecf8d94d5bb6443680d7b2c3f1
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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