Water → HCID 57925850, compound

HRID 1013459Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([P:13]2(=[O:20])[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.CN([CH:26]=[O:27])C.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(C(C)C)C(C)C.[OH2:66]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:19][N:16]1[CH2:17][CH2:18][P:13]([C:10]2[CH:11]=[CH:12][C:7]([C:26]([OH:27])=[O:66])=[CH:8][CH:9]=2)(=[O:20])[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 70 °C

Procedure

4-(1-Methyl-4-oxido-1,4-azaphosphinan-4-yl)phenyl trifluoromethanesulfonate (0.18 g, 0.50 mmol) was made 0.25 M in 4:1 DMF:water and to this stirring solution was added palladium acetate (7 mg, 0.03 mmol), and DPPP (25 mg, 0.06 mmol). The resulting mixture was thoroughly degassed with bubbling carbon monoxide for 20 mins. DIPEA (130 mg, 1.01 mmol) was added and a CO balloon was attached. The resulting mixture was stirred at 70° C. for 16 h. The mixture was then cooled to ambient temperature and carried onto the subsequent reaction without purification. MS: cal'd 254 (MH+), exp 254 (MH+).

Workup

customThe resulting mixture was thoroughly degassed with bubbling carbon monoxide for 20 mins
temperatureThe mixture was then cooled to ambient temperature
customcarried onto the subsequent reaction without purification

Sources & evidence

ORD record: ord-4eb4ea28a38f40c697ac28b12f553c3b
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981874B2

Reaction notes

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