Ammonia → HCID 57825143, compound

HRID 1668729Notes

Reaction equation

HRID 1668729 reaction equation
II.[Br:3][C:4]1[CH:5]=[C:6]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:15]([CH3:24])[CH:14]=2)=[CH2:12])[CH:7]=[CH:8][C:9]=1[F:10].[NH3:25].C([O:29][CH2:30]C)(=O)C.C(#[N:34])C>C(OCC)(=O)C.[Ag]OC#N>[NH2:25][C:30]1[O:29][CH2:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])=[C:15]([CH3:24])[CH:14]=2)([C:6]2[CH:7]=[CH:8][C:9]([F:10])=[C:4]([Br:3])[CH:5]=2)[N:34]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 21930812Acetonitrile ethyl acetateHCID 57825247HCID 57825247, compound

Product 1

HCID 57825143HCID 57825143, compound

Reagents, catalysts & solvents 2

HCID 178513473HCID 178513473, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

According to general method 2, a solution of iodine in ethyl acetate was added to a mixture of methanesulfonic acid 4-[1-(3-bromo-4-fluoro-phenyl)-vinyl]-2-methyl-phenyl ester (1400 mg, 3.6 mmol) and silver cyanate 1.1 eq in ethyl acetate/acetonitrile. The crude product of this reaction was subsequently reacted with aqueous ammonia (30% by vol). Purification by SCX followed by silica column (dichloromethane/methanol, 95:5) yield 650 mg of product (40%).

Workup

  1. customPurification by SCX

Sources & evidence

ORD record
ord-7c3db03aea7d412480c1213d363164fd
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

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