Sodium Carbonate → 2-Tert-butoxycarbonylamino-5-(2-tert-butylaminosulfonyl-phenyl)-phenyl carbamic acid tert-butyl ester

HRID 1433177Notes

Reaction equation

HRID 1433177 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:9]=1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:4])([CH3:3])[CH3:2].[C:24]([NH:28][S:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O)(=[O:31])=[O:30])([CH3:27])([CH3:26])[CH3:25].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd]Cl.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.[Fe+2]>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[C:12]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2[S:29]([NH:28][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:30])=[O:31])[CH:11]=[CH:10][C:9]=1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 130078031,2-Di(tert-Butyloxycarbonylamino)-4-bromobenzene

Product 1

HCID 579350332-Tert-butoxycarbonylamino-5-(2-tert-butylaminosulfonyl-phenyl)-phenyl carbamic acid tert-butyl esterYield 100.9%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (5-bromo-2-tert-butoxycarbonylamino-phenyl)-carbamic acid tert-butyl ester (4.0 g, 10.3 mmol), 2-(tert-butylaminosulfonyl)-phenyl boronic acid (5.3 g; 20.6 mmol), PdCl2 dppf (1.7 g, 0.20 mmol) and 1M Na2CO3 solution (83 mL, 82.7 mmol) in 1,2-dimethoxyethane was heated to 90° C. for 12 h under inert atmosphere. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (silica, EtOAc: hexanes, 3:7) to afford the title compound as a yellow viscous oil (5.4 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 8.14 (m, 1H), 7.88 (m, 1H), 7.43-7.69 (m, 6H), 7.19 (m, 1H), 7.28 (m, 1H), 1.52 (s, 9H), 1.48 (s, 9H), 1.06 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C26H37N3O6S: 520.65 (M+H), Found 520.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by chromatography (silica, EtOAc: hexanes, 3:7)

Sources & evidence

ORD record
ord-6f821a3a4b0e40c78dc39b986c1f4f43
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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