Phosgene → HCID 57786672, compound

HRID 1969118Notes

Reaction equation

HRID 1969118 reaction equation
[CH3:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:17].[CH:18]([N:21]([CH:24]([CH3:26])C)[CH2:22]C)([CH3:20])C.C(Cl)(Cl)=[O:28].N1CCCC1>ClCCl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:7]([B:8]2[O:12][C:11]([CH3:13])([CH3:14])[C:10]([CH3:16])([CH3:15])[O:9]2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:17][C:22]([N:21]1[CH2:18][CH2:20][CH2:26][CH2:24]1)=[O:28]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 467380052-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 57786672HCID 57786672, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of 2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (233 mg, 1.00 mmol) in 6 mL of dichloromethane were added 0.52 mL (3.00 mmol) of diisopropylethylamine and 0.55 mL of a 20% solution of phosgene in toluene at 0 C. The reaction mixture was stirred at 0 C for 10 minutes and pyrrolidine was added. The reaction mixture was stirred at 0 C for 1 hour then applied to column chromatography without workup. Chromatography (20->50% in hexanes/ethyl acetate in 20 minutes->100% in 30 minutes) gave 195 mg (0.591 mmol, 59%) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 0 C for 1 hour

Sources & evidence

ORD record
ord-3311921e5ae8435092362b8b6ce229d2
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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