Dimethyl Ether → HCID 70565636, compound

HRID 2179366Notes

Reaction equation

[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[C:20]([OH:38])[C:21]4[O:30][C:29]5[CH2:28][CH2:27][N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][C:24]=5[C:22]=4[CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[O:5])[CH3:2].[CH3:39]OC>>[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([C:18]3[CH:19]=[C:20]([O:38][CH3:39])[C:21]4[O:30][C:29]5[CH2:28][CH2:27][N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][C:24]=5[C:22]=4[CH:23]=3)(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)=[O:5])[CH3:2]

Participants

Reactant 2

HCID 8254Dimethyl Ether

HCID 68109201HCID 68109201, compound

Product 1

HCID 70565636HCID 70565636, compoundYield 82%

Procedure

The product of step C was converted to the methyl ether derivative following the procedure of Example 54, step B. Purification by flash column chromatography (SiO2, 75:25 hexane/ethyl acetate) provided tert-butyl 8-((1-(ethoxycarbonyl)-1H-indol-5-yl)sulfonyl)-6-methoxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (25 mg, 82%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.30 (d, J=8.7 Hz, 1H), 8.23 (d, J=1.8 Hz, 1H), 7.88 (dd, J=8.7, 1.8 Hz, 1H), 7.73 (d, J=3.6 Hz, 2H), 7.35 (s, 1H), 6.69 (d, J=3.6 Hz, 1H), 4.60-4.45 (m, 4H), 4.03 (s, 3H), 3.88-3.74 (m, 2H), 2.95-2.75 (m, 2H), 1.50 (s, 9H), 1.47 (t, J=7.2 Hz, 3H).

Workup

customPurification by flash column chromatography (SiO2, 75:25 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-9a47db5776c24cab8912d0d111774933
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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