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Methyl chloroformate → Dimethyl (6-acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-yl)imidodicarbonate

HRID 510848
Notes
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Reaction equation

HRID 510848 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:6]([C:15](=[O:17])[CH3:16])[CH:5]=[C:4]([Cl:18])[C:3]=1[CH3:19].C(N(CC)C(C)C)(C)C.Cl[C:30]([O:32][CH3:33])=[O:31]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:15]([C:6]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:2]([N:1]([C:30]([O:32][CH3:33])=[O:31])[C:30]([O:32][CH3:33])=[O:31])[C:3]([CH3:19])=[C:4]([Cl:18])[CH:5]=1)(=[O:17])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6586Methyl chloroformate2×HCID 81531DiisopropylethylamineHCID 583684301-(6-Amino-4-chloro-3'-fluoro-5-methylbiphenyl-2-yl)ethanone

Product 1

HCID 86666778Dimethyl (6-acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-yl)imidodicarbonateYield 79.1%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(6-amino-4-chloro-3′-fluoro-5-methylbiphenyl-2-yl)ethanone (100 mg, 0.4 mmol) in methylene chloride (2 mL) was added N,N-diisopropylethylamine (0.094 mL, 0.54 mmol) followed by methyl chloroformate (0.033 mL, 0.43 mmol). The mixture was stirred at room temperature for 30 min. To the reaction mixture was added a catalytic amount of DMAP and another equivalent of methyl chloroformate. The reaction was stirred at room temperature over a weekend, quenched with water and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate, then concentrated. The residue was purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the bis-acylated product (67 mg, 50%). LCMS calculated for C19H18ClFNO5 (M+H)+: m/z=394.1. found: 394.1.

Workup

  1. stirringThe reaction was stirred at room temperature over a weekend
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel
  8. washeluting with 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-fe361792f05d41a0a50f7aa95c9eec21
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096600B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes