Triethylamine → HCID 24993725, compound

HRID 1673233Notes

Reaction equation

HRID 1673233 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]3[O:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH:17]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]3=[CH:10][C:9]=2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[C:4]([Cl:35])[CH:3]=1.CCN(CC)CC>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Cl:35][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[C:8]1[N:13]=[C:12]2[O:14][C:15]([CH3:27])([CH3:26])[CH2:16][CH:17]([NH:18][C:19]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:25])[C:11]2=[CH:10][C:9]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:19]([O:20][CH3:21])=[O:25]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 71072739HCID 71072739, compound

Product 1

HCID 24993725HCID 24993725, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 887MethanolSolvent

Procedure

A solution of Example 314 (840 mg, 1.45 mmol), palladium(II) acetate (16.3 mg, 0.07 mmol), dppf (81 mg, 0.15 mmol), and NEt3 (405 μL, 2.90 mmol) in 20 mL of CH3OH was stirred at 100° C. under 50 psi of CO for 24 h. After cooling to rt, the reaction mixture was filtered. The filtrate was concentrated and chromatography on a Biotage 25+M cartridge using 1:1 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.46 (s, 3H), 1.49 (s, 9H), 1.54 (s, 3H), 1.82 (m, 1H), 2.29 (dd, J=6.2, 13.3, 1H), 3.90 (s, 3H), 4.89 (br. s, 1H), 5.12 (m, 1H), 7.01 (d, J=8.5, 2H), 7.16 (d, J=8.4, 2H), 7.40 (m, 1H), 7.73-7.92 (m, 3H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3e5ce9edaf6e453883db641ebb30d78d
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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