Dimethyl Ether → HCID 68108870, compound

HRID 2179434Notes

Reaction equation

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

Participants

Reactant 2

HCID 8254Dimethyl Ether

HCID 68109611HCID 68109611, compound

Product 1

HCID 68108870HCID 68108870, compoundYield 78%

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, 17:3 hexane/ethyl acetate) provided tert-butyl 6-methoxy-8-phenoxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (20 mg, 78%) as a colorless oil: 1H NMR (CDCl3, 400 MHz) δ 7.36-7.29 (m, 2H), 7.11-7.04 (m, 1H), 7.02-6.95 (m, 2H), 6.63 (s, 1H), 6.56 (d, J=2.0 Hz, 1H), 4.46 (s, 2H), 4.00 (s, 3H), 3.82 (s, 2H), 2.86 (s, 2H), 1.50 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 17:3 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-bea7cc080da4475b81fc37b2c86721a5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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