HCID 44242721, compound → HCID 57930414, compound

HRID 2198345Notes

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-4f6bb7bebdff47e28d36b0a3d07fe56a
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338447B2

Reaction notes

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