(Diethylamino)sulfur trifluoride → HCID 178490694, compound

HRID 76272Notes

Reaction equation

[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][C:13](O)([CH3:15])[CH3:14])/[C:7](=[N:17]/[C:18](=[O:28])[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])/[S:6]1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:35])CC>C(Cl)Cl>[C:1]([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][C:13]([F:35])([CH3:15])[CH3:14])/[C:7](=[N:17]/[C:18](=[O:28])[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])/[S:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

The product from Example 80 (50 mg, 0.12 mmol) in CH2Cl2 (4 mL) was treated with DAST (38 mg, 0.24 mmol) at −78° C. The mixture was stirred at −78° C. for 1.5 hrs, quenched with saturated aqueous NaHCO3 and extracted with CH2Cl2 (2×). The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 29 mg (58%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.38 (d, J=21.48 Hz, 6 H) 1.65 (s, 9 H) 1.68-1.80 (m, 2 H) 1.81-1.93 (m, 2 H) 2.84 (t, J=7.67 Hz, 2 H) 3.91 (s, 3 H) 6.91 (d, J=8.90 Hz, 1 H) 7.33 (dd, J=8.59, 2.76 Hz, 1 H) 7.97 (s, 1 H) 8.11 (d, J=2.76 Hz, 1 H); MS (DCI/NH4+) m/z 427 (M+H)+.

Workup

customquenched with saturated aqueous NaHCO3
extractionextracted with CH2Cl2 (2×)
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-4179e5f8c89843db9a57e02f4bce2858
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835475B2

Reaction notes

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