Trimethylsilyl iodide → HCID 76684540, compound

HRID 925221Notes

Reaction equation

C(OC([N:7]1[CH2:28][CH2:27][C:11]2[C:12]3[C:13]([CH3:26])([CH3:25])[CH2:14][CH2:15][C:16]=3[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:18][C:10]=2[CH2:9][CH2:8]1)=O)CC.[Si](I)(C)(C)C>C(Cl)(Cl)Cl>[CH3:25][C:13]1([CH3:26])[C:12]2[C:11]3[CH2:27][CH2:28][NH:7][CH2:8][CH2:9][C:10]=3[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:16]=2[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 60 °C

Procedure

Into a glass vial containing the product from step (b) (71 mg, 0.195 mmol) dissolved in CHCl3 (2 ml), TMSI (266 μL, 1.95 mmol) was added. The reaction mixture was heated to 60° C. for 4 hours. The volatiles were evaporated in vacuo and the residue was dissolved in 2M HCl (3 ml) and water (20 ml). The aqueous mixture was washed with diethyl ether (2×). The aqueous layer was then basified with 2M NaOH to pH 10 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo gave the crude product. Purification by preparative reverse phase HPLC gave the title compound as a colorless oil (9.9 mg). 1H NMR (300 MHz, CDCl3) δ 8.66 (bs, 1H); 7.41-7.26 (m, 5H); 7.00 (s, 1H); 3.31-3.15 (m, 8H); 2.84 (t, J=7.5 Hz, 2H); 1.89 (t 7.2 Hz, 2H); 1.33 (s, 6H); MS: ESI (positive): 328 (M+H).

Workup

customThe volatiles were evaporated in vacuo
dissolutionthe residue was dissolved in 2M HCl (3 ml)
washThe aqueous mixture was washed with diethyl ether (2×)
extractionextracted with DCM (3×)
washThe combined DCM extracts were washed with brine
dry with materialdried over Na2SO4, and solvent
customevaporated in vacuo
customgave the crude product
customPurification by preparative reverse phase HPLC

Sources & evidence

ORD record: ord-4e58f05a4fe54d44bd0ede1ead081576
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284277B2

Reaction notes

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