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Pentane → 1H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 1-[tris(1-methylethyl)silyl]-

HRID 2043691
Notes
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Reaction equation

HRID 2043691 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[C:5]2=[N:6][CH:7]=1.[Li]C(C)(C)C.CCCCC.[CH:31](N1CCCCC1)=[O:32].[NH4+].[Cl-]>C1COCC1.CCCCCC.CCOCC>[CH:12]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[N:8]1[C:5]2=[N:6][CH:7]=[C:2]([CH:31]=[O:32])[CH:3]=[C:4]2[CH:10]=[CH:9]1)([CH3:14])[CH3:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 8003PentaneHCID 174291-PiperidinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 242292235-Bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 497590861H-Pyrrolo[2,3-B]pyridine-5-carboxaldehyde, 1-[tris(1-methylethyl)silyl]-
Yield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Bromide x254 (1.1 g, 3.11 mmol) is dissolved in freshly distilled absolute THF (40 ml). A 1.7 M solution of t-BuLi in pentane (1.92 ml, 1.05 eq) is added dropwise at −100° C. under vigorous stirring in a flow of argon. The reaction mixture is stirred for 45 min and meanwhile allowed to heat up slowly to −78° C. After this, a solution of N-formylpiperidine (0.42 g, 1.2 eq, 3.73 mmol) in freshly distilled absolute THF (5 ml) is added dropwise for 5 min. The mixture is allowed to heat up to 0° C. under stirring in the cooling bath, and then poured into a mixture of saturated aqueous NH4Cl (20 ml) and 1:1 hexane/ether mixture (100 ml). The organic phase is separated, dried with anhydrous sodium sulfate, and evaporated. The residue is purified by chromatography on silicagel, CCl4/MeCN) to afford 0.7 g of 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde x255.

Workup

  1. stirringThe reaction mixture is stirred for 45 min
  2. temperatureto heat up to 0° C.
  3. stirringunder stirring in the cooling bath
  4. customThe organic phase is separated
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue is purified by chromatography on silicagel, CCl4/MeCN)

Sources & evidence

ORD record
ord-4d9ed09fa2f147dfb2a918527bc9bd4a
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08586623B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes