Water → HCID 66649106, compound

HRID 418670

Reaction equation

HRID 418670 reaction equation
[Br-].[CH3:2][N:3]([CH3:25])[CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li][CH2:27]CCC.[F:31][C:32]1[CH:49]=[C:48]([N+:50]([O-:52])=[O:51])[CH:47]=[CH:46][C:33]=1[O:34][C:35]1[CH:40]=[CH:39][N:38]=[C:37]2[CH:41]=[C:42]([CH:44]=O)[S:43][C:36]=12.O>C1COCC1>[F:31][C:32]1[CH:49]=[C:48]([N+:50]([O-:52])=[O:51])[CH:47]=[CH:46][C:33]=1[O:34][C:35]1[CH:40]=[CH:39][N:38]=[C:37]2[CH:41]=[C:42]([CH:44]=[CH:27][CH2:5][CH2:4][N:3]([CH3:25])[CH3:2])[S:43][C:36]=12

Participants

6

Reactant 4

HCID 962WaterHCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 58790381HCID 58790381, compoundHCID 178418339Butyllithium

Product 1

HCID 66649106HCID 66649106, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-(dimethylamino)ethyl)triphenylphosphonium bromide (680 mg, 1.54 mmol) in THF (7.7 mL) was added n-BuLi (2.5M in hexanes, 0.65 mL, 1.62 mmol) dropwise at 0° C., the resulting mixture was warmed to room temperature and stirred for 30 min. 7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine-2-carbaldehyde 233 (500 mg, 1.17 mmol) was added in one portion and the mixture was stirred for 2 h. The mixture was poured into water, extracted with EtOAc; the organic phase was extracted with 3% citric acid, the combined aqueous phase was basified to pH˜11 by the addition of 1N NaOH. It was then extracted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure affording title compound 234 (360 mg, 0.929 mmol, 78% yield) as a crude mixture that was used in the next step without further purification. MS (m/z): (M+1) 388.1 (100%).

Workup

  1. stirringthe mixture was stirred for 2 h
  2. extractionextracted with EtOAc
  3. extractionthe organic phase was extracted with 3% citric acid
  4. additionthe combined aqueous phase was basified to pH˜11 by the addition of 1N NaOH
  5. extractionIt was then extracted with EtOAc
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f25b001b2a64c3e8267dba57ab6b7cf
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

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