4-Iodoaniline → HCID 71059597, compound

HRID 405225Notes

Reaction equation

HRID 405225 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:37]=O)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1.[I:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:37][NH:44][C:43]2[CH:45]=[CH:46][C:40]([I:39])=[CH:41][CH:42]=2)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1

Participants

6

Reactant 3

HCID 108934-IodoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674276HCID 86674276, compound

Product 1

HCID 71059597HCID 71059597, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

Solid NaBH(OAc)3 (1.3 g, 6.0 mmol) was added to a DCM solution (6 mL) of methyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate (1.0 g, 3.0 mmol) and 4-iodoaniline (723 mg, 3.3 mmol), and the resulting mixture was stirred at room temperature. After 3 h the resulting mixture diluted with DCM and saturated aqueous Na2CO3 and the layers were separated. The aqueous phase was extracted with DCM and the combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography

Sources & evidence

ORD record
ord-a0f71a7530504487883432a8c5f27f63
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

Loading…