Thionyl Chloride → HCID 10251696, compound

HRID 1916633Notes

Reaction equation

HRID 1916633 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]3[CH:21]=[C:22]4[C:27](=[CH:28][CH:29]=3)[CH:26]=[C:25]([CH2:30]O)[CH:24]=[CH:23]4)=[N:16][CH:17]=2)=[CH:8][CH:7]=1.C([O-])(O)=O.[Na+].[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18]#[C:19][C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([CH2:30][N:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[CH:26]=4)[CH:21]=3)=[N:16][CH:17]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 67363454HCID 67363454, compound

Product 1

HCID 10251696HCID 10251696, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

58 μL (0.80 mmol) thionyl chloride are added at 0° C. to a solution of 148 mg (0.40 mmol) {6-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-naphthalen-2-yl}-methanol in 5 mL DCM. The solution is heated to RT and stirred for 1 h at this temperature. The reaction mixture is diluted with 30 mL DCM, combined with ice water, made alkaline with saturated NaHCO3 solution and the organic phase is washed with water. The organic phase is dried over MgSO4 and filtered. 0.10 mL (1.20 mmol) pyrrolidine are added to the filtrate, which is stirred for 2 h at RT and for 1 h at 40° C. The solvent is eliminated i.vac. and the purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH/NH3 5:1:0.1).

Workup

  1. washthe organic phase is washed with water
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. stirringis stirred for 2 h at RT and for 1 h at 40° C
  5. customand the purification

Sources & evidence

ORD record
ord-e780540744f843ce8eb57b1b7ecb5d9e
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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