Phosgene → HCID 57786802, compound

HRID 1969124Notes

Reaction equation

HRID 1969124 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][C:6]1[C:11]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:21].C(N(C(C)C)CC)(C)C.Cl.[F:32][C:33]([F:45])([F:44])[CH:34]([C:40]([F:43])([F:42])[F:41])[O:35][CH:36]1[CH2:39][NH:38][CH2:37]1>ClCCl>[CH3:5][C:6]1[C:11]([B:12]2[O:16][C:15]([CH3:17])([CH3:18])[C:14]([CH3:20])([CH3:19])[O:13]2)=[CH:10][CH:9]=[CH:8][C:7]=1[NH:21][C:1]([N:38]1[CH2:39][CH:36]([O:35][CH:34]([C:33]([F:32])([F:44])[F:45])[C:40]([F:43])([F:41])[F:42])[CH2:37]1)=[O:2]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 81531DiisopropylethylamineHCID 467380052-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86632802HCID 86632802, compound

Product 1

HCID 57786802HCID 57786802, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Phosgene (20% in toluene, 0.26 mL, 0.49 mmol) was added to a solution of 2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (0.096 g, 0.411 mmol) and diisopropylethylamine (0.29 mL, 1.7 mmol) in 4 mL of dichloromethane at 0-5° C. The reaction mixture was then stirred at RT for 30 min., then transferred via Pasteur pipette to a flask containing 3-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-azetidine hydrochloride prepared as in the above example (0.41 mmol). A total of 6 mL of additional dichloromethane was used in rinsing. The very pale yellow solution was stirred for 18.5 h. 10 g of silica gel was added, and the mixture was concentrated to a white powder. Column chromatography (0->50% EtOAc/hexanes) afforded 0.117 g (59%) of 3-(2,2,2-trifluoro-1-trifluoromethyl-ethoxy)-azetidine-1-carboxylic acid [2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amide as a colorless oil.

Workup

  1. customtransferred via Pasteur pipette to a flask
  2. additioncontaining
  3. washin rinsing
  4. stirringThe very pale yellow solution was stirred for 18.5 h
  5. addition10 g of silica gel was added
  6. concentrationthe mixture was concentrated to a white powder

Sources & evidence

ORD record
ord-8ed62d2eb9a1471f8c59692b926d2138
Source dataset
uspto-grants-2013_04
Patent number
US08426441B2

Reaction notes

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