Phenylboronic Acid → HCID 68071556, compound

HRID 1961459Notes

Reaction equation

HRID 1961459 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.FC1C=CC(CN[C:34](C2C(C(F)(F)F)=NC3C(C=2)=CC=CN=3)=[O:35])=CC=1>>[CH3:34][O:35][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 66827Phenylboronic AcidHCID 11983730tert-butyl N-(1-(4-bromophenyl)ethyl)carbamateHCID 46908968HCID 46908968, compound

Product 1

HCID 68071556HCID 68071556, compound

Procedure

The title compound was synthesized from tert-Butyl 1-(4-bromophenyl)ethylcarbamate and phenyl boronic acid, following the general procedure for the coupling of aryl bromides with boronic acids (see above and c.f. scheme 27). Purification was done by flash column chromatography using Pet. ether/EtOAc 5:1→100% EtOAc as eluent. The fractions containing product were further purified by size exclusion chromatography Sephadex LH20, CHCl3/MeOH 1:1 yielding the title compound (68%).

Workup

  1. customPurification
  2. additionThe fractions containing product
  3. customwere further purified by size exclusion chromatography Sephadex LH20, CHCl3/MeOH 1:1 yielding the title compound (68%)

Sources & evidence

ORD record
ord-045ecb1ef0a24fcfa41593af84ce38e7
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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