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5-Bromo-2-methoxybenzaldehyde → (5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanol

HRID 896084
Notes
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Reaction equation

HRID 896084 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[N:6][CH:7]=1.[Li]CCCC.[Br:22][C:23]1[CH:24]=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=[O:29]>C1COCC1.CCCCCC>[Br:22][C:23]1[CH:24]=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:28]([C:2]2[CH:7]=[N:6][C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=3[F:16])=[CH:4][CH:3]=2)[OH:29])[CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 906845-Bromo-2-methoxybenzaldehydeHCID 22349574(5-Bromo-pyridin-2-yl)-(2,4-difluoro-phenyl)-amineHCID 178418339Butyllithium

Product 1

HCID 22349592(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanolYield 40.7%

Reagents, catalysts & solvents 2

HCID 8028Tetrahydrofuran
Solvent
2×
HCID 8058HexaneSolvent

Procedure

(5-Bromo-pyridin-2-yl)-(2,4-difluoro-phenyl)-amine (100 mg; 0.35 mmol) in THF (2.2 ml) is treated at −78 C with nBuLi (0.48 ml of a 1.5M solution in hexane; 0.77 mmol). After 10 min at −78 C, 5-bromo-2-methoxybenzaldehyde (75 mg; 0.35 mmol) in THF (0.3 ml) is added and stirring continued for 30 min. at −78 C. The reaction mixture is poured on water/ice and extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated to dryness. Purification via chromatography (SiO2; TBME/hexanes 3/7) yields the title compound (60 mg; 40%)

Workup

  1. additionThe reaction mixture is poured on water/ice
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. customevaporated to dryness
  5. customPurification via chromatography (SiO2; TBME/hexanes 3/7)

Sources & evidence

ORD record
ord-1a1e0c750b814880950b4bbccde2676d
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06919336B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes