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Iodine → 4-(5-fluoro-2-methoxyphenyl)-2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 1522008
Notes
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Reaction equation

HRID 1522008 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:15]=[C:16]([C:17]#[N:18])[C:9]=23)[CH:7]=1.C([N-]C(C)C)(C)C.[Li+].[I:37]I>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[C:15]([I:37])=[C:16]([C:17]#[N:18])[C:9]=23)[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 904136554-(5-fluoro-2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 904128114-(5-fluoro-2-methoxyphenyl)-2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
3×

Conditions

Temperature
-75 °C

Procedure

A solution of Example 248B (0.7 g, 1.76 mmol) in tetrahydrofuran (50 mL) was cooled to −75° C. and treated dropwise with 2N lithium diisopropylamide in tetrahydrofuran (1.7 mL, 3.40 mmol). The mixture was stirred at −75° C. for 30 minutes and iodine (0.85 g, 3.52 mmol) in 2.5 mL tetrahydrofuran was added. The mixture was slowly brought to room temperature and quenched with aqueous ammonium chloride (100 mL) and extracted with ethyl acetate (twice). The organic layers were concentrated and purified by column chromatography (Combi Flash Rf) (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 524 (M+H)+.

Workup

  1. customwas slowly brought to room temperature
  2. customquenched with aqueous ammonium chloride (100 mL)
  3. extractionextracted with ethyl acetate (twice)
  4. concentrationThe organic layers were concentrated
  5. custompurified by column chromatography (Combi Flash Rf) (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-cb38fa9446e24e90a1338f83bad414b5
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes