Phenol → HCID 68109648, compound

HRID 2179364Notes

Reaction equation

Cl[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]([S:22]([C:25]2[CH:26]=[C:27]3[C:31](=[CH:32][CH:33]=2)[N:30](C(OCC)=O)[CH:29]=[CH:28]3)(=[O:24])=[O:23])[CH:3]=1.C1([OH:45])C=CC=CC=1>>[NH:30]1[C:31]2[C:27](=[CH:26][C:25]([S:22]([C:4]3[CH:3]=[C:2]([OH:45])[C:7]4[O:8][C:9]5[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:11][C:10]=5[C:6]=4[CH:5]=3)(=[O:24])=[O:23])=[CH:33][CH:32]=2)[CH:28]=[CH:29]1

Participants

Reactant 2

HCID 996Phenol

HCID 68109418HCID 68109418, compound

Product 1

HCID 68109648HCID 68109648, compoundYield 65%

Procedure

The product of step A was converted to the phenol derivative using the procedure of Example 54, step A. Purification by flash column chromatography (SiO2, 3:7 hexane/ethyl acetate) provided tert-butyl 8-((1H-indol-5-yl)sulfonyl)-6-hydroxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (90 mg, 65%) as a yellow solid: 1H NMR (CDCl3, 400 MHz) δ 8.98 (s, 1H), 8.22 (s, 1H), 7.77-7.17 (m, 4H), 6.51 (s, 1H), 4.49 (s, 2H), 3.80-3.67 (m, 2H), 2.80-2.63 (m, 2H), 1.49 (s, 9H).

Workup

customPurification by flash column chromatography (SiO2, 3:7 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-c15cff80b35a4f248e2cf18d37dcdf75
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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