Tri-o-tolylphosphine → HCID 118276549, compound

HRID 1053660Notes

Reaction equation

HRID 1053660 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@:12]([CH3:20])([CH2:18]I)[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[CH3:29])[NH2:25].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[Zn]>[NH2:25][C:24]1[CH:23]=[CH:22][C:28]([CH3:29])=[C:27]([CH2:18][C@@:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])([CH3:20])[CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:26]=1

Participants

5

Reactant 3

HCID 80271Tri-o-tolylphosphineHCID 1188893-Iodo-p-toluidineHCID 118276557HCID 118276557, compound

Product 1

HCID 118276549HCID 118276549, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

Following the General Procedure of Description 15 (Part B), the zinc insertion product of (9c) is used in situ to cross couple with commercial 3-iodo-4-methyl-aniline (466 mg, 2.0 mmol) in the presence of tris(benzylideneacetone)dipalladium (Pd2(dba)3) (46 mg, 0.05 mmol, 2.5 mol-%) and tris(o-tolyl)phosphine (P(o-tol)3) (60 mg, 0.20 mmol, 10 mol-%) in anhydrous degassed DMF (6 mL). Filtration, aqueous work-up, and purification by silica gel column chromatography furnish the title compound (9d).

Workup

  1. customin anhydrous degassed DMF (6 mL)
  2. filtrationFiltration, aqueous work-up, and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-c87d21912759418fbbfcec5d4c0883bc
Source dataset
uspto-grants-2016_07
Patent number
US09394237B2

Reaction notes

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