tert-Butyl 4-chloro-3-formylpyridin-2-ylcarbamate → HCID 86710396, compound

HRID 1398408Notes

Reaction equation

HRID 1398408 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[C:4]([F:18])[CH:3]=1.Cl[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:21]=1[CH:34]=[O:35]>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[C:21]=2[CH:34]=[O:35])=[C:4]([F:18])[CH:3]=1

Participants

3

Reactant 2

HCID 46204204tert-Butyl 4-chloro-3-formylpyridin-2-ylcarbamateHCID 59126908HCID 59126908, compound

Product 1

HCID 86710396HCID 86710396, compoundYield 76%

Procedure

Prepared as described in Example 17, Part C by Suzuki coupling between 2-(4-chloro-2,5-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) preparation described in Example 14, Part A) and tert-butyl 4-chloro-3-formylpyridin-2-ylcarbamate (Preparation described in Example 17, Part B) to afford tert-butyl 4-(4-chloro-2,5-difluorophenyl)-3-formylpyridin-2-ylcarbamate (3.7 g, 8.91 mmol, 76% yield) as a yellow solid. LC/MS (ESI) m/e 367.1 [(m)−, calcd for C17H16ClF2N2O3 367.1] LC/MS retention time (method E): tR=1.07 min.

Workup

  1. customPrepared
  2. custompreparation

Sources & evidence

ORD record
ord-cea151914d354c28beab8379882349ea
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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