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Water → 4-Chloro-1-(toluene-4-sulfonyl)-2-tributylstannanyl-1H-pyrrolo[2,3-b]pyridine

HRID 506779
Notes
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Reaction equation

HRID 506779 reaction equation
[Li+].CC([N-]C(C)C)C.[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:17]=[CH:18][C:11]=12.[Sn:29](Cl)([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33].O>C1COCC1.CCOC(C)=O>[Cl:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16]([S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[C:17]([Sn:29]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:18][C:11]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 2724682Lithium diisopropylamideHCID 81672684-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 594326124-Chloro-1-(toluene-4-sulfonyl)-2-tributylstannanyl-1H-pyrrolo[2,3-b]pyridineYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Add LDA (1.5 equiv., 0.74 mL, 1.47 mmol) dropwise in the space of 5 min to azaindole 25 (0.3 g, 0.98 mmol) in THF (15 mL), stirred at −78° C., under N2. After stirring the reaction medium for 0.5 h, add Bu3SnCl dropwise (475 mg, 400 μL, 1.47 mmol) and stir the reaction medium for a further 0.5 h. Then allow the reaction medium to return to room temperature, stop the reaction with H2O, dilute with EtOAc (200 mL), wash with brine, dry (MgSO4) and concentrate. The residue is submitted to flash chromatography to give 26 (0.46 g, 79%) as a colorless oil: 1H NMR (CDCl3) δ 8.15 (d, 1H, J=5.1 Hz), 7.97 (dd, 2H, J=8.0, 1.5 Hz), 7.27 (d, 2H, J=8.4 Hz), 7.09 (d, 1H, J=5.2 Hz), 6.75 (s, 1H), 2.36 (s, 3H), 1.65-1.20 (m, 12H), 0.93 (t, 9H), TLC (EtOAc at 40%/heptane) Rf=0.65.

Workup

  1. stirringAfter stirring the reaction medium for 0.5 h
  2. stirringstir the reaction medium for a further 0.5 h
  3. customto return to room temperature
  4. washwash with brine
  5. dry with materialdry (MgSO4)
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-4b647f6a64d8407f8fc0b084d1c5fb66
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786114B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes