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Allyltributylstannane → 2-(3-allyl-6-chloropyridin-2-yl)-4-fluoro-1H-indole

HRID 595713
Notes
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Reaction equation

HRID 595713 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[C:20]([F:23])[CH:19]=[CH:18][CH:17]=3)=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1)(=O)=O.[CH2:26]([Sn](CCCC)(CCCC)CCCC)[CH:27]=[CH2:28].[Li+].[Cl-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:28]([C:7]1[C:8]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[C:20]([F:23])[CH:19]=[CH:18][CH:17]=3)=[N:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH:27]=[CH2:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 903335466-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate

Product 1

HCID 903339482-(3-allyl-6-chloropyridin-2-yl)-4-fluoro-1H-indoleYield 68.4%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-yl trifluoromethanesulfonate (2 g, 5.1 mmol), allyltributylstannane (2 g, 6.1 mmol) and anhydrous LiCl (256 mg, 6.1 mmol) in THF (30 mL), Pd(PPh3)4 (588 mg, 0.51 mmol) was added under N2 protection. The reaction mixture was stirred at 60° C. overnight. After it was concentrated in vacuo, the residue was purified by column chromatography (PE:EA=400:1˜100:1) to give the product of 2-(3-allyl-6-chloropyridin-2-yl)-4-fluoro-1H-indole (1 g, yield: 68%). 1H-NMR (CDCl3, 400 MHz) δ 9.72 (s, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.12˜7.24 (m, 3H), 7.02 (s, 1H), 6.77 (t, J=8.0 Hz, 1H), 6.04˜6.12 (m, 1H), 5.25 (d, J=10.0 Hz, 1H), 5.13 (d, J=17.2 Hz, 1H), 3.74 (d, J=6.0 Hz, 2H). MS (M+H)+: 287/289.

Workup

  1. additionwas added under N2 protection
  2. concentrationAfter it was concentrated in vacuo
  3. customthe residue was purified by column chromatography (PE:EA=400:1˜100:1)

Sources & evidence

ORD record
ord-e417a7062404406d8dfaeaf6d78ba335
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09243002B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes