HCID 44242721, compound → HCID 57930414, compound

HRID 1775959Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)(O)[CH3:13])[C:6]1[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:5]2=1>S(=O)(=O)(O)O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](/[CH:11]=[C:12](/[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)\[CH3:13])[C:6]1[CH2:22][N:23]([CH3:26])[CH2:24][CH2:25][C:5]2=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-(6-chloro-2-methyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)-2-(4-fluorophenyl) propan-2-ol (30 mg, 0.0806 mmol) was dissolved in 25% sulfuric acid, and the reaction mixture was heated overnight at 60° C. The reaction was monitored by TLC. After completion of the reaction, pH of the reaction mixture was adjusted to 10-12 and extracted with ethyl acetate. The organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude compound was purified by preparative TLC. The pure compound was stirred in ethanolic HCl to yield HCl salt of (E)-6-chloro-9-(2-(4-fluorophenyl)prop-1-enyl)-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (8 mg). 1H NMR (CD3OD):—7.63-7.70 (m, 2H), 7.60 (s, 1H), 7.10-7.20 (m, 3H), 7.0 (s, 1H), 4.65 (d, 1H), 4.43 (d, 1H), 3.78-3.90 (m, 1H), 3.52-3.60 (m, 2H), 3.10-3.25 (m, 5H), 1.96 (s, 3H).

Workup

customAfter completion of the reaction, pH of the reaction mixture
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude compound was purified by preparative TLC

Sources & evidence

ORD record: ord-98427fdf172340dc8bcc93a124aaf24e
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260429B2

Reaction notes

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