Triethylamine → Diethyl 4-(amino(4-methoxyphenyl)methyl)phenylphosphonate

HRID 1525202Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[NH2:9])=[CH:4][CH:3]=1.[P:18]([O-])([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19].CCN(CC)CC>C1(C)C=CC=CC=1.[NH4+].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:9][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:5]1[CH:6]=[CH:7][C:2]([P:18](=[O:19])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of (4-bromophenyl)(4-methoxyphenyl)methanamine, 1-1-c, (2 g, 6.8 mmol), diethyl phosphate (1.1 g, 8.2 mmol) and Et3N (1.3 g, 10.2 mmol) in toluene (25 ml) was added Pd(PPh3)4 (1.5 g, 20%). The mixture was allowed to stir for two days at 100° C. The mixture was then diluted with saturated NH4Cl and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated, and purified over silica gel (5% MeOH/DCM) to obtain as an oil, 1-1-d, (1.00 g). 1HNMR (300 MHZ, DMSO-d): 1.29 (m, 6H), 3.77 (s, 3H), 4.10 (m, 4H), 5.19 (s, 1H), 6.82 (d, 2H), 7.26 (d, 2H), 7.48 (d, 2H), 7.74 (d, 2H).

Workup

extractionextracted with EtOAc
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
custompurified over silica gel (5% MeOH/DCM)
customto obtain as an oil, 1-1-d, (1.00 g)

Sources & evidence

ORD record: ord-573068b2f55a400aa5fc31f9466916fb
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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