Bicarbonate Ion → HCID 59322133, compound

HRID 1401706Notes

Reaction equation

[C:1]([N:3]1[C:11]2[CH:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[C:5]2[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][C:4]1=2)#[CH:2].Cl.Br[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(=O)(O)[O-]>O>[CH3:17][N:14]1[CH2:15][CH2:16][C:4]2[N:3]([C:1]#[C:2][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[C:11]3[CH:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=3[C:5]=2[CH2:13]1

Participants

Conditions

Temperature: 99 °C

Procedure

A mixture of 5-ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (138 mg, 0.6 mmol), 4-bromopyridinehydrochloride (100 mg, 0.51 mmol), dichlorobistriphenylphosphine palladium (II) (10 mg, 0.015 mmol) and TBAF.3H2O (481 mg, 1.5 mmol) was heated at 50° C. (observed exothermic temperature was 99° C.) for 5 min by microwave. After completion of reaction (monitored by TLC&LCMS), the mixture was poured into water (20 mL), saturated bicarbonate was added, and the mixture extracted with EtOAc (3×20 mL). The organic layer was washed with water (2×20 mL), dried over sodium sulfate and concentrated under vacuum to obtain 170 mg of 2,8-dimethyl-5-pyridin-4-ylethynyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm): 8.58 (d, 2H), 7.42 (d, 1H), 7.34 (d, 2H), 7.20 (s, 1H), 7.10 (d, 1H), 3.62 (s, 2H), 3.08 (m, 2H0, 3.92 (m, 2H), 2.60 (s, 3H0, 2.42 (s, 3H).

Workup

customAfter completion of reaction (monitored by TLC&LCMS)
additionwas added
extractionthe mixture extracted with EtOAc (3×20 mL)
washThe organic layer was washed with water (2×20 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-bb486bc0e7294447b54319d627a3d08c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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