Water → HCID 67379216, compound

HRID 1499071Notes

Reaction equation

HRID 1499071 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:15]([CH3:17])=[CH:14][C:13]([CH3:18])=[CH:12][C:11]=3[C:10]3[CH2:19][N:20]([CH3:23])[CH2:21][CH2:22][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.[N:24]1[CH:29]=CC(B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+].O.CO[CH2:42][CH2:43]OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:23][N:20]1[CH2:21][CH2:22][C:9]2[N:8]([C:4]3[CH:3]=[CH:43][CH:42]=[C:6]([C:7]4[CH:26]=[CH:25][N:24]=[CH:29][CH:2]=4)[CH:5]=3)[C:16]3[C:15]([CH3:17])=[CH:14][C:13]([CH3:18])=[CH:12][C:11]=3[C:10]=2[CH2:19]1

Participants

7

Reactant 5

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 67378919HCID 67378919, compound

Product 1

HCID 67379216HCID 67379216, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

To a de-aerated solution of 5-(3-bromophenyl)-2,6,8-trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (80 mg, 0.217 mmol), pyridine-4-boronic acid (53 mg, 0.431 mmol) and K2CO3 (116 mg, 0.845 mmol) in DME (4 mL)-water (2 mL) was added Pd(PPh3)4 (12 mg, 0.013 mmol). The reaction mixture was heated at 90° C. for 45 min. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in EtOAc (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain crude, which was purified by reverse phase HPLC to yield 2,6,8-trimethyl-5-(3-(pyridin-4-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (TFA salt, CD3OD) δ (ppm): 8.78 (d, 2H), 8.1 (m, 3H), 7.9 (m, 1H), 7.8 (t, 1H), 7.6 (m, 1H), 7.2 (s, 1H), 6.8 (s, 1H), 4.76 (m, 1H), 4.4 (m, 1H), 3.8 (m, 1H), 3.5 (m, 1H), 3.1 (s, 3H), 2.8-3.03 (m, 2H), 2.4 (s, 3H), 1.93 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (50 mL)
  3. washwashed with water (20 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain crude, which
  7. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d583d065ab55472089c6fb657e2fc097
Source dataset
uspto-grants-2015_12
Patent number
US09199985B2

Reaction notes

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