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Nitrogen → HCID 117777431, compound

HRID 64141
Notes
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Reaction equation

HRID 64141 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.N#N.[C:17]1([S:23]([N:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28](B3OC(C)(C)C(C)(C)O3)=[CH:27]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N+:8]([C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([C:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:26]([S:23]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:25])=[O:24])[CH:27]=2)[CH:7]=1)([O-:10])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 10658908N-(3-bromo-5-nitrophenyl)acetamideHCID 162179451-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product 1

HCID 117777431HCID 117777431, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of N-(3-bromo-5-nitrophenyl)acetamide (0.38 g, 1.48 mmol) in 1,2-dimethoxyethane (15 ml) was degassed by N2 bubbling for 5 min. 1-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (0.68 g, 1.77 mmol, 1.2 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.12 g, 0.148 mmol, 0.1 eq.) and aqueous sodium carbonate (0.47 g, 4.45 mmol, 3.0 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was purified by column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to give the product in 77% yield (0.5 g).

Workup

  1. customthe mixture was degassed for another 5 min
  2. customThe crude residue of the product was purified by column chromatography (60-120 silica gel, 30% ethyl acetate in hexane)
  3. customto give the product in 77% yield (0.5 g)

Sources & evidence

ORD record
ord-e3349ae2be6b4d3e92ee90610e34da6e
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447091B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes