Dimethylformamide → HCID 9883037, compound

HRID 1450247Notes

Reaction equation

HRID 1450247 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17](Br)=[CH:16][N:15]=3)[CH:10]=2)[S:5][CH2:4][CH2:3]1.C([Li])(C)(C)C.CN(C)[CH:29]=[O:30].[NH4+].[Cl-]>CCOCC.CCCCC>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[C:13][C:14]3[CH:19]=[CH:18][C:17]([CH:29]=[O:30])=[CH:16][N:15]=3)[CH:10]=2)[S:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 19975512HCID 19975512, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 9883037HCID 9883037, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled (-78° C.) solution of 358 mg (1.0 mmol) of 2-(4,4-dimethylthiochroman-6-yl)ethynyl-5-bromopyridine in 5 ml of anhydrous ether was added slowly under nitrogen 1.3 ml of 1.7M (2.21 mmol) tert-butyl lithium in pentane. The mixture was stirred at -78° C. for 1 h and then treated with 95 mg (1.3 mmol) of anhydrous dimethylformamide. The mixture was stirred at -78° C. for a further 0.5 hours, then warmed to 0° C. and treated with 5 ml of saturated NH4Cl solution followed by 5 ml of ether. The organic layer was separated and the aqueous layer was extracted with ether. The organic layers were combined, washed successively with water and saturated NaCl solution and then dried (MgSO4). The solvent was then removed in vacuo and the residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes) followed by high pressure liquid chromatography (Whatman M-9 Partisil 10/50 column, 15% ethyl acetate in hexanes) to give the title compound as a pale yellow solid.

Workup

  1. stirringThe mixture was stirred at -78° C. for a further 0.5 hours
  2. temperaturewarmed to 0° C.
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ether
  5. washwashed successively with water and saturated NaCl solution
  6. dry with materialdried (MgSO4)
  7. customThe solvent was then removed in vacuo
  8. customthe residue purified by flash chromatography (silica; 15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c8dab1309ecc492d80d6266feef74df6
Source dataset
uspto-grants-1997_02
Patent number
US05602130

Reaction notes

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