Triethylamine → HCID 118101228, compound

HRID 708841Notes

Reaction equation

Br[C:2]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][C:3]=1[CH2:4][N:5]([CH3:13])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].CCN(CC)CC.[P:33]([O-:40])([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:22]([O:21][C:19]([NH:18][C:15]1[CH:16]=[CH:17][C:2]([P:33]([O:37][CH2:38][CH3:39])([O:34][CH2:35][CH3:36])=[O:40])=[C:3]([CH:14]=1)[CH2:4][N:5]([CH3:13])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 105 °C

Procedure

A solution of 12B (25 mg, 0.060 mmol), bis(tri-t-butylphosphine)palladium (0) (3.08 mg, 6.02 μmol), Et3N (0.042 mL, 0.301 mmol) and diethyl phosphite (0.039 mL, 0.301 mmol) in toluene (0.6 mL) was degassed with Ar by evacuating and filling (4×). The sealed vessel was stirred for 2 days at 105° C. The reaction mixture was concentrated and purified by column chromatography (0 to 30% EtOAc in hexanes) to yield 12C (15 mg, 0.032 mmol, 52.7% yield).

Workup

customby evacuating
concentrationThe reaction mixture was concentrated
custompurified by column chromatography (0 to 30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-da81ac6b8e064a87b6dc8cb1c8dcd58e
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174974B2

Reaction notes

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