Skatole → HCID 68109613, compound

HRID 2179334Notes

Reaction equation

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

Participants

Reactant 2

HCID 6736Skatole

HCID 86667995HCID 86667995, compound

Product 1

HCID 68109613HCID 68109613, compoundYield 32%

Procedure

The product of Example 41, step B was reacted with 3-methylindole following the procedure of Example 41, step C providing tert-butyl 8-(3-methyl-1H-indol-1-ylsulfonyl)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (36 mg, 32%) as a clear oil: 1H NMR (CDCl3, 300 MHz) δ 8.02 (m, 2H), 7.74 (d, J=8.7 Hz, 1H), 7.42 (t, J=8.4 Hz, 2H), 7.34 (s, 1H), 7.30 (dd, J=8.4, 1.3 Hz, 1H), 7.21 (dt, J=3.7, 1.0 Hz, 1H), 4.53 (br s, 2H), 3.80 (br s, 2H), 2.84 (br s, 2H), 2.22 (s, 3H), 1.51 (s, 9H).

Sources & evidence

ORD record: ord-096ab232b2bf473aa62c584cd68f0fc4
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067949B2

Reaction notes

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