Phenyl thioxochloroformate → thiocarbonic acid O-[(4-cyano-3-fluoro-phenyl)-pyridin-3-yl-methyl]Ester O-phenyl Ester

HRID 1594877Notes

Reaction equation

[F:1][C:2]1[CH:9]=[C:8]([CH:10]([OH:17])[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:18]1[CH:23]=[CH:22][C:21]([O:24][C:25](Cl)=[S:26])=[CH:20][CH:19]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:21]1([O:24][C:25](=[S:26])[O:17][CH:10]([C:8]2[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-fluoro-4-(hydroxy-pyridin-3-yl-methyl)-benzonitrile (as described in Example 20, Step C) (0.4 g, 1.75 mmol) in CH2Cl2 (25.0 mL) at 0° C. was added phenyl thionochloroformate (0.388 mL, 2.8 mmol) and DMAP (0.471 g, 3.86 mmol). The solution was stirred at 25° C. for 3 hr. The reaction was partitioned with saturated NaHCO3 and CH2Cl2. The CH2Cl2 layer was washed with brine, dried with MgSO4, and evaporated in vacuo to obtain the title compound after chromatography (silica gel, CH2Cl2:MeOH 99:1).

Workup

customThe reaction was partitioned with saturated NaHCO3 and CH2Cl2
washThe CH2Cl2 layer was washed with brine
dry with materialdried with MgSO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-2ecd332d1ad9473293e2c1d0cf52f3e0
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284755B1

Reaction notes

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