Water → HCID 49779838, compound

HRID 1773254Notes

Reaction equation

[CH3:1][N:2]1[CH:15]([CH3:16])[CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[OH-].[K+].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:28])=[CH2:27])=[CH:22][N:21]=1.O>CN1C(=O)CCC1>[CH3:1][N:2]1[CH:15]([CH3:16])[CH2:14][C:5]2[N:6]([CH2:27][CH:26]([C:23]3[CH:22]=[N:21][C:20]([CH3:19])=[CH:25][CH:24]=3)[CH3:28])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

A flask was charged with 2,3,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (117 mg, 0.5 mmol) and KOH (392 mg, 7 mmol) in NMP (2 mL) and heated at 140° C. for 10 min. The mixture was cooled to 0° C. and to it was added 2-methyl-5-(prop-1-en-2-yl)pyridine (199 mg, 1.5 mmol) dropwise. The mixture was heated at 140° C. for 2 h. The progress of the reaction was monitored by LCMS (5% conversion). The mixture was cooled to RT, water was added and the mixture filtered and evaporated. The solid obtained was purified by HPLC. 1HNMR (CD3OD, TFA salt) d (ppm): 8.10 (m, 2H), 7.60 (m, 1H), 7.22 (s, 1H), 7.10 (d, 1H), 6.96 (d, 1H), 4.62 (m, 1H), 4.38 (m, 2H), 4.22 (m, 2H), 3.50 (m, 2H), 3.0 (s, 3H), 2.80 (s, 3H), 2.40 (s, 3H), 1.60-1.30 (m, 7H).

Workup

temperatureThe mixture was cooled to 0° C. and to it
temperatureThe mixture was heated at 140° C. for 2 h
temperatureThe mixture was cooled to RT
filtrationthe mixture filtered
customevaporated
customThe solid obtained
customwas purified by HPLC

Sources & evidence

ORD record: ord-f1ac1432e976493faac5fb964bec2bab
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255094B2

Reaction notes

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