Methanesulfonyl chloride → HCID 59394371, compound

HRID 1971370Notes

Reaction equation

HRID 1971370 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[C:19]3[C:14](=[C:15]([F:29])[C:16]([O:20][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([CH2:27][OH:28])[CH:22]=4)=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH3:30])=[O:10])=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32].[CH3:35][S:36](Cl)(=[O:38])=[O:37]>ClCCl.[NH4+].[Cl-]>[F:29][C:15]1[C:16]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]([CH2:27][O:28][S:36]([CH3:35])(=[O:38])=[O:37])[CH:22]=2)=[CH:17][CH:18]=[C:19]2[C:14]=1[CH:13]=[C:12]([CH3:30])[N:11]2[C:9](=[O:10])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:31]([F:33])([F:32])[F:34])[CH:4]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59394779HCID 59394779, compound

Product 1

HCID 59394371HCID 59394371, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

4-Fluoro-5-(2-hydroxymethyl-pyridin-4-yloxy)-2-methyl-indole-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (370 mg, 0.775 mmol) is placed in dichloromethane (10 mL) and methanesulfonyl chloride (0.15 mL, 1.92 mmol) and TEA (0.4 ml, 2.87 mmol) are added. The reaction is stirred at rt for 20 min before being diluted with dichloromethane and saturated aqueous NH4Cl. The aqueous layer is extracted further with dichloromethane. The combined organic layers are washed with brine and dried over Na2SO4, filtered, and concentrated to give the title compound. MS (ESI) m/z 555.8 (M+1)

Workup

  1. extractionThe aqueous layer is extracted further with dichloromethane
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d833ce098b7b44eb86f6a40ad8bc4606
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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