Diiodomethane → HCID 11515504, compound

HRID 1822186Notes

Reaction equation

[CH2:1]([Zn]CC)C.C(O)(C(F)(F)F)=O.C(I)I.[CH2:16]([N:23]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([Cl:37])[CH:31]=1)[CH:24]([CH2:27][CH:28]=[CH2:29])[CH2:25][OH:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH2:16]([N:23]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[C:32]([Cl:37])[CH:31]=1)[CH:24]([CH2:27][CH:28]1[CH2:1][CH2:29]1)[CH2:25][OH:26])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

Diethylzinc (0.064 g, 0.526 mmol) was added to a flask containing CH2Cl2 (2 mL) at 0° C. A solution of TFA (0.052 ml, 0.526 mmol) in CH2Cl2 (1 ml) was slowly added to the flask containing diethylzinc over 20 min. A solution of CH2I2 (0.042 mL, 0.526 mmol) in CH2CH2 (1 mL) was added next over 20 min. followed by addition of 2-[benzyl(3-chloro-4-fluorophenyl)amino]pent-4-en-1-ol (7-5, 0.028 g, 0.088 mmol) in CH2Cl2 (1 mL). The resulting solution was warmed to 25° C. The reaction mixture was diluted with NaHCO3 (sat. aq) and extracted with CH2Cl2 (3×5 ml). The combined organic layers were dried with NaSO4, filtered, and concentrated. The crude residue was purified by reverse phase liquid chromotography (Semi Prep YMC C-18 Reverse Phase Column 5% CH3CN/H2O to 95% CH3CN/H2O with 0.1% TFA present) to yield 2-[benzyl(3-chloro-4-fluorophenyl)amino]-3-cyclopropylpropan-1-ol (9-2). MS 334.2 found 334.8 (M+H+) required.

Workup

extractionextracted with CH2Cl2 (3×5 ml)
dry with materialThe combined organic layers were dried with NaSO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by reverse phase liquid chromotography (Semi Prep YMC C-18 Reverse Phase Column 5% CH3CN/H2O to 95% CH3CN/H2O with 0.1% TFA present)

Sources & evidence

ORD record: ord-41ada9e77efa4c71850ea63c3a62d883
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608739B2

Reaction notes

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