HCID 10104703, compound → HCID 57527217, compound

HRID 1452955Notes

Reaction equation

HRID 1452955 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[S:13][CH2:12][CH2:11][CH2:10][S:9]1.[Li]CCCC.[CH:19]([NH:22][C:23]1[S:24][C:25]2[CH:31]=[C:30]([CH:32]=[O:33])[CH:29]=[CH:28][C:26]=2[N:27]=1)([CH3:21])[CH3:20].CCOC(C)=O.CCCCCC>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH:32]([C:30]2[CH:29]=[CH:28][C:26]3[N:27]=[C:23]([NH:22][CH:19]([CH3:20])[CH3:21])[S:24][C:25]=3[CH:31]=2)[OH:33])[S:9][CH2:10][CH2:11][CH2:12][S:13]1

Participants

6

Reactant 4

HCID 10104703HCID 10104703, compoundHCID 21226206Ethyl acetate hexaneHCID 57527235HCID 57527235, compoundHCID 178418339Butyllithium

Product 1

HCID 57527217HCID 57527217, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2-fluorophenyl)-1,3-dithiane (0.820 g, 3.83 mmol) in THF (25 mL) was added n-BuLi (1.6 M in hexane, 2.3 mL, 3.68 mmol) at −10° C. over 10 min. The resulting solution was stirred at −10° C. for 30 min before a solution of 2-(isopropylamino)benzo[d]thiazole-6-carbaldehyde (0.385 g, 1.75 mmol) in THF (5 mL) was added. The mixture was stirred at between −10° C. and 5° C. for 2.5 hr, and then quenched with saturated NH4Cl solution (25 mL). This was extracted with AcOEt (3×20 mL). The combined extract was washed with brine and dried over anhydrous MgSO4. The title compound (0.563 g, 74% yield) was isolated as a pale yellow solid by silica gel chromatography (35% AcOEt/hexane).

Workup

  1. additionwas added
  2. customquenched with saturated NH4Cl solution (25 mL)
  3. extractionThis was extracted with AcOEt (3×20 mL)
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-0e12d226433c44fe92a908f943c3c2f4
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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