Isocyanatocyclopropane → 1-Cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 1626659Notes

Reaction equation

HRID 1626659 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([B:13]2[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]2)=[C:9]([F:22])[CH:8]=1)=[O:5])[CH3:2].F[C:24]1C=C(C=CC=1B1OC(C)(C)C(C)(C)O1)N.C1(N=C=O)CC1>>[CH:1]1([NH:3][C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([B:13]3[O:14][C:15]([CH3:21])([CH3:20])[C:16]([CH3:19])([CH3:18])[O:17]3)=[C:9]([F:22])[CH:8]=2)=[O:5])[CH2:24][CH2:2]1

Participants

4

Reactant 3

HCID 637659IsocyanatocyclopropaneHCID 447552073-Fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 666787871-Ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×

Product 1

HCID 666792291-Cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaYield 100%

Procedure

Prepared as 1-ethyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 28) using 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline and cyclopropyl isocyanate as starting materials. The crude reaction mixture was then partitioned between DCM and water. The organic layer was recovered, passed through a hydrophobic frit and the solvent removed in vacuo to yield a light orange solid (3.2 g, 10 mmol, 100%).

Workup

  1. customThe crude reaction mixture
  2. customwas then partitioned between DCM and water
  3. customThe organic layer was recovered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f0ba7958473346a9bc1cb03b06536f22
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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