Triethylamine → HCID 57965691, compound

HRID 1673261Notes

Reaction equation

HRID 1673261 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:18])[CH:16]=[CH2:17])([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C.[NH4+].[Cl-]>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:18])/[CH:16]=[CH:17]/[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 707414-BromobenzaldehydeHCID 20786195HCID 20786195, compound

Product 1

HCID 57965691HCID 57965691, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of (2-acryloylamino-phenyl)-carbamic acid tert-butyl ester (20.0 g, 76.3 mmol), 4-bromobenzaldehyde (14.4 g, 77.8 mmol), Pd2(dba)3 (0.56 g, 0.61 mmol), tri-o-tolyphosphine (0.370 g, 1.22 mmol) and triethylamine (42.1 mL, 0.300 mol) in DMF (300 mL) was stirred at 100 degrees Celsius under N2 for 5 hours. The reaction mixture was allowed to cool down to room temperature and poured into a saturated aqueous solution of NH4Cl. The precipitate was filtered off and washed with water, dried in vacuo at 40° C. overnight. The crude product was purified by flash column chromatography to obtain a yellow solid (15.5 g, 56%). MS: calc'd 367 (MH+), exp 367 (MH+). 1H NMR (d6-DMSO, 400 MHz) δ 10.0 (s, 1H), 9.79 (s, 1H), 8.53 (s, 1H), 7.98 (d, 2H, J=8.0 Hz), 7.87 (d, 2H, J=8.0 Hz), 7.68 (d, 1H, J=16 Hz), 7.60 (m, 2H), 7.14 (m, 2H), 7.10 (d, 1H, J =16 Hz), 1.46 (s, 9H).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried in vacuo at 40° C. overnight
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-909a3a4332cb4680a65229ac120d8367
Source dataset
uspto-grants-2011_08
Patent number
US07999000B2

Reaction notes

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