Dichloromethane → (3-Tert-butoxycarbonylamino-2'-methanesulfonyl-biphenyl-4-yl)-carbamic acid tert-butyl ester

HRID 1433190Notes

Reaction equation

HRID 1433190 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].[CH3:24][S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1B(O)O)(=[O:27])=[O:26].C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.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]>[C:19]([O:18][C:16](=[O:17])[NH:15][C:9]1[CH:10]=[CH:11][C:12]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[S:25]([CH3:24])(=[O:27])=[O:26])=[CH:13][C:8]=1[NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:23])([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27735392-(Methylsulfonyl)phenylboronic AcidHCID 130078031,2-Di(tert-Butyloxycarbonylamino)-4-bromobenzene

Product 1

HCID 57935002(3-Tert-butoxycarbonylamino-2'-methanesulfonyl-biphenyl-4-yl)-carbamic acid tert-butyl esterYield 86%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (5-bromo-2-tert-butoxycarbonylamino-phenyl)-carbamic acid tert-butyl ester (Example 1, Step A, 8.81 g, 0.0385 mol), 2-methylsulfonylphenylboronic acid (10.00 g, 0.0500 mol), Pd(dppf)Cl2.CH2Cl2 (4.71 g, 0.0578 mmol), and Na2CO3 (24.46 g, 0.116 mol) in 1,2-dimethoxyethane (200 mL) and water (50 mL) was heated 80° C. for 12 hours 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, 1:2) to afford the title compound as a yellow oil (15.30 g, 86%).

Workup

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

Sources & evidence

ORD record
ord-645fa1f850754c7f897fb80305295720
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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