Acetic Acid → 4-(4-Fluoro-2-iodo-phenylamino)-cyclohexanecarboxylic acid ethyl ester

HRID 1685396Notes

Reaction equation

HRID 1685396 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.[CH2:10]([O:12][C:13]([CH:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1)=[O:14])[CH3:11].C(O)(=O)C.C(O[BH3-])(=O)C.[Na+]>C(Cl)Cl>[CH2:10]([O:12][C:13]([CH:15]1[CH2:20][CH2:19][CH:18]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=2[I:9])[CH2:17][CH2:16]1)=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 27782834-Fluoro-2-iodoanilineHCID 23670382Sodiumacetoxyborohydride

Product 1

HCID 672929454-(4-Fluoro-2-iodo-phenylamino)-cyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-fluoro-2-iodoaniline and (18 g) 4-oxo-cyclohexanecarboxylic acid ethyl ester (20 g) in DCM (200 ml) is added acetic acid (4.4 ml) and 4 Å molecular sieves (5 g). After 2 h at rt, sodium acetoxyborohydride (50 g) is added and the suspension stirred overnight. The reaction is made slightly alkaline with KHCO3/NaHCO3(aq) and extracted with DCM to give crude 4-(4-fluoro-2-iodo-phenylamino)-cyclohexanecarboxylic acid ethyl ester.

Workup

  1. extractionextracted with DCM

Sources & evidence

ORD record
ord-f60e4aaa58d84ad886c60c1c44daba63
Source dataset
uspto-grants-2012_04
Patent number
US08148403B2

Reaction notes

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