Indole → HCID 68109573, compound

HRID 2179343Notes

Reaction equation

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

Participants

Reactant 2

HCID 798Indole

HCID 86667996HCID 86667996, compound

Product 1

HCID 68109573HCID 68109573, compoundYield 45%

Procedure

The product of step B and indole were reacted using the procedure of Example 41, step C to provide tert-butyl 8-(1H-indol-1-ylsulfonyl)-6-chloro-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (35 mg, 45%) as an off-white solid: 1H NMR (CDCl3, 300 MHz) δ 8.00 (d, J=8.1 Hz, 1H), 7.89 (s, 1H), 7.73 (d, J=1.5 Hz, 1H), 7.58 (d, J=3.6 Hz, 1H), 7.52 (d, J=7.8 Hz, 1H), 7.36-7.30 (m, 1H), 7.25-7.20 (m, 1H), 6.69-6.68 (m, 1H), 4.52 (s, 2H), 3.80 (t, J=5.4 Hz, 2H), 2.88 (t, J=5.1 Hz, 2H), 1.50 (s, 9H).

Sources & evidence

ORD record: ord-cbcf3aef46884645844ffea1b5af9aed
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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